United States

From Boston to Bar Harbor: a New England road trip [+Map]

May 24, 2019
This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

This New England road trip itinerary will take you on the scenic route from Boston to Portland then to Maine’s Mid Coast and Acadia National Park. You’ll experience the east coast food – like lobster and seafood – and take in the beautiful Maine lighthouses that still guide the ships along the rocky coastline. Find an interactive map at the bottom of this post.



Hey there – this post likely contains affiliate links, which means I earn a commission (at no extra cost to you) if you purchase from them. This helps me earn a few dollars to run this website. For more info, check out my terms here


This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

When the Women in Travel Conference announced that they would be heading to Portland, Maine for their three-day summit, I immediately started planning for an epic New England road trip along the coastal regions. While I’ve crossed Maine off of the places I’ve been – I drove through it when I did an east coast road trip a couple of years back – I never did get to the coast.

The summit was the perfect excuse to explore more of Maine’s incredible coast. While this was not the exact itinerary I took – since I did spend three days at a conference – this guide is how I would split up my trip if I did not have a conference to attend.

What you need to know about New England

Portland's colourful buildings | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

New England is one of the oldest colonial regions in the United States, comprising of six states in the northeastern section of the country. Spanning from Maine to Vermont, New Hampshire, Massachusetts, Rhode Island and Connecticut.

Known as the birthplace of colonial America, New England is now home to nearly 15 million people. The area is known for its hills (with part of the Appalachians running through it) and for its rugged, unforgiving coastline. Because it is so far north compared to the rest of the USA, I find that its climate is similar to the east coast of Canada.

That means winters are long and snowy, and the summers are short but popular with visitors. Fall is peak season for New England when millions of visitors come to the region to take in the fall colours. In spring, the trees are in bloom. The coastal areas of Maine are just waking up for the season in spring, and many attractions open in mid to late May, around the American Memorial Day holiday.

New England is made up of 38 different regions. This New England road trip itinerary focuses on only four, Metro Boston, Southern Maine/ Portland, Mid-Coast and Acadia/ Down East.


Get your free Travel Budget Planner | My Wandering Voyage travel blog

How to get from Boston to Bar Harbor

Amtrack Downeaster | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Unless you have a car yourself and can drive the whole route, my suggestion is to wait until day five or six of this New England road trip itinerary to rent a car and here’s why: Boston is hazardous even to walk. Seriously, you’ve got to keep your eyes peeled at all times, and I would not wish driving in the city on anyone. However, it’s very walkable and has a public transportation system to get you from point A to point B.

You can then take the Amtrack Downeaster to Portland. It takes 2h 30m, and it’s a lovely train trip up the coast. After a couple of days in Portland, you’ll want to rent a car for the rest of the way to hit all the lighthouses and lobster shacks on the way to Acadia National Park.

Take the coastal scenic route

Acadia National Park | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

A majority of this New England road trip will take you along the United States Route 1, the longest north-south route in the US.

Route 1 takes you from the Canada-US border in Maine to the tip of the Florida Keys. While you won’t be travelling all 3,818km (2,369 miles) on this New England road trip, you’ll be taking the scenic route through Maine’s Mid Coast, stopping at various small coastal towns and beautiful lighthouses.

If you’d rather zip from Portland to Acadia National Park without stopping, then take the I-95.


RELATED: 10 treasures to discover in New Brunswick


Two nights in Boston

The first stop you’re going to make on a New England road trip is in Boston. Whether you can drive up or fly in, spending at least two nights in this historic city is a must. Boston is the epicentre for cultural activities and historical architecture. And the best part is it is all walkable.

Day one: Land in Boston, explore the downtown

Boston row houses | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

There is so much to see in Boston, but two full days will help you get the lay of the land and see some of the best of what Boston has to offer. On day one, you’ll land in Boston and explore the city’s most famous neighbourhood: Beacon Hill.

Next up is the Downtown, where you’ll find history lurking behind every corner and enjoy Boston’s little central park, the Boston Common. Start your morning off right at a coffee shop and later, dig into some of the best grilled cheese in Boston.

What to see

Beautiful Acorn Street, Beacon Hill, Boston | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Beacon Hill and Acorn Street: Is it even a trip to Boston if you don’t visit the city’s most famous neighbourhood? Beacon Hill is where Boston was settled by colonials back in the 1600s and is known for its redbrick row houses and stunning façades.

There was an actual signal from which Beacon Hill got its name. You might be surprised to hear that it was not a great place to live for several centuries before it was gentrified in the 19th century. Make sure to visit Acorn Street, the most photographed street in the US, early in the morning, since you’ll want to capture the morning light on the stunning cobblestone street and red brick houses.

Massachusetts State House: This golden domed building, located on the outskirts of Beacon Hill, is where the seat of government is in Massachusetts. Dating back to 1798, this building is actually the second statehouse in Boston. Inside is filled with history and traditions dating back to the beginning of the country, so it’s definitely worth a tour!

Massachusetts State House seen from Boston Common | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage  #Boston #Portland #Maine #travel

Boston Common and Public Gardens: Opposite the state house is the Boston Common and Public Gardens, Boston’s central park. It’s the oldest city park in the US, where you can sit and relax, stroll along the many pathways, watch people play a game of baseball, visit the site of the Great Elm, throw a coin into the Brewer Fountain, or catch a musical performance at the bandstand.

The Public Garden sits adjacent to the Boston Common. There, you’ll find a pond, several flowerbeds, statues and a trail. Sit on one of the park benches, like the one Robin Williams used to sit by or jump into a Swan Boat in the summertime. Don’t miss the little ducks in the bronze statue called Make Way for Ducklings. People like to dress up the ducks in different outfits. They were little judges when I was there.

Granbury cemetery Boston | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Boston’s Freedom Trail: The Freedom Trail is a 4km pathway through the heart of Boston’s downtown that stops at 16 historically significant locations. You can do the trail yourself, or take a tour to soak in all the history. On the trail, you’ll see the Granary Burying Grounds, Massachusetts State House, King’s Chapel, The Old Corner Bookstore, Old State House, Boston Massacre Site, Faneuil Hall, the U.S.S. Constitution and more.

The Boston Globe: As a journalist, I had to stop and see the home of the (new) Boston Globe building. (Have you seen Spotlight?!) It’s located in Exchange Place, which is built with the facades of the old stock exchange building.

Fan Pier Park overlooking Boston | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Fan Pier Park: If you want lovely views of the Boston skyline, then cross the bridge to Fan Pier Park, on the way you’ll see Boston’s old swing bridge, which closed to pedestrians in 2014. Walk along the pier and then turn around to see the marvellous Boston cityscape.

Boston Tea Party Museum: This floating museum allows you to re-live some of the critical moments of US history and take a peek into what life was like during the American Revolution.

Where to eat

Tatte Bakery and Café: Grab your breakfast at this adorable cafe; one location is located right on Beacon Hill. I suggest a delicious chai latte and a morning bun, a sweet pastry that tastes like a cinnamon bun and a croissant had a baby.

Quincy Market, Boston | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Quincy Market: Located near the Faneuil Hall, Quincy Market is this marvel of a building. It houses hundreds of shops from food to clothes to keepsakes. Along the middle of the market, you’ll find so many food options that exist only here. Try the Boston Chowdah or the baked beans that gave Boston its nickname: Beantown.

Thinking Cup: End your first night in Boston at the Thinking Cup, a bistro near the Boston Common. They have so many incredible sandwich options, but I suggest building your own grilled cheese – it’s to die for!

Day two: Explore Back Bay and Fenway Park

Buoys in Boston | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Day two of this New England road trip itinerary will take you into Boston’s Back Bay neighbourhood and Fenway Park. Back Bay is a beautiful area known for its stunning residential architecture, New England’s tallest buildings and shopping districts. Walk along the green space, called Commonwealth Avenue Mall, between Commonwealth Ave’s streets. 

What to see

Women’s Memorial and history trail: Women had (and still have, obviously) a huge part in the shaping of Boston. Often overshadowed by the influential white men at the time, we are starting to understand the role that women have played in history. It is so important that we don’t lose these accounts. The Boston Women’s Memorial is a sculpture in the Commonwealth Avenue Mall that depicts Phillis Wheatley, Abigail Adams, and Lucy Stone. This memorial is one of the stops on the Boston Women’s Heritage Trail – an important experience in this historical city.

Trinity Church: Likely one of the most famous churches in Boston’s Back Bay area, Trinity Church has been a staple of the skyline since it was built in the 1700s. You can take a self-guided tour of the church or go on a guided tour ($10 or free on Sundays). The building itself has been on American Association of Architects list of top 10 buildings in the United States for centuries.

Boston Public Library: Not only is the Boston Public Library the third largest public library in the United States, but it is one of the most historic. It was founded back in the mid-1800s. Today you can visit the central branch for free on your own or a public tour. Make sure to check out the Grand Staircase, Bates Hall, the courtyard and the various galleries.

Sky Walk observatory: If you’ve read any of my other posts, then you know I love to get views from above. Boston has one of those birds-eye views of the city at the Prudential Center. It costs $21 USD, which includes the ride up and down, an audio tour, the Dreams of Freedom exhibit and a multi-media movie theatre.

Mapparium: Probably one of the coolest experiences is at the Mapparium at the Mary Baker Eddy Library in Back Bay. You get to walk inside a three-story tall globe made of stained glass. It was built in 1935 and shows the world as it was at the time (notice how some of the political borders and names have changed).

Fenway Park: Known as “America’s most beloved ballpark,” Fenway Park is home to the Major League Baseball team Boston Red Sox. Not only is it the oldest MLB ballpark in the United States, but it’s more than just a place to watch a game. You can take a behind the scenes tour of Fenway Park to get the insider details of how the place operates. Tours take you on a 60 minute guided walk. If you don’t have the time, you can take a 15-minute tour that brings you to the archives, a roof-top deck and ends with a panoramic view of the stadium. There are also other tour options based on what you would like to see in Fenway. You can buy tickets online up to 30 days before the date, after that you can chance getting a ticket at the door.

Where to eat

Brunch at Sonsie: With all this walking, you’ll want to stop for a bite to eat. Why not a delicious spot for brunch? Sonsie is a classy bistro known for its brunch. From seafood to pancakes to sandwiches to eggs, their menu will please just about everyone.

Seafood at Saltie Girl: When on the east coast, you have to dig into the local cuisine, which means seafood! They create every fish and seafood dishes that you could imagine, from smoked fish to seafood towers to fried lobster and waffles.

Where to stay in Boston

HI Boston Hostel | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Budget – HI Boston Hostel: While the price of this hostel is higher than I’ve paid for a dorm bed, I can’t deny how much I enjoyed the HI Boston. Not only was it cozy and clean with beautiful décor, but the staff was incredibly friendly. Plus it had great WiFi and a delicious free breakfast.

Midrange – The Revolution Hotel: Boston is not cheap to stay. Their mid-range prices are more like luxury prices, and you’ll generally find cheaper hotels the further you stay out of the downtown. The Revolution Hotel is a trendy boutique hotel outside the city centre and offers a cool meeting/ working space called Conspire.

Luxury – The Godfrey Hotel Boston: This hotel is as fancy as it gets in Boston. From beautiful décor to the location right in the heart of the city, I’m sure you’ll enjoy your stay at the Godfrey Hotel.

Three nights in Portland

There are so many reasons why you need to visit Portland, Maine. Not only is it the craft brew capital of the United States, but the city has been named the 2018 restaurant city of the year. With over 200 establishments calling Portland home, it isn’t any wonder that there are more restaurants per capita than any other city in the US (except San Francisco). Trust me; you’re going to love it here.

Day three: arrive in Portland, brew bus tour

Portland Old Port | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

After taking the Amtrak Downeaster from Boston to Portland, you’re going to get settled before jumping on the Brew Bus. Trust me; you’re going to want to sample as many places as possible. Then take a bite into your first lobster dish.

What to see

Disclosure: I was invited by the Maine Brew Bus on one of their tours through the Women in Travel Summit conference. All opinions are my own.

Hardshore Distillery, Portland, Maine | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Maine Brew Bus: Let me just say that I’m not a big drinker. I’ll enjoy a cocktail or two every once, and a while and I love Ontario cider, but it’s very rare for me to actually have a drink. And beer is just out of the question. But I had the opportunity to go on a brew tour through the Women in Travel Summit, and I can honestly say it has changed my perspective on drinks.

Not only was our driver and host hella funny, but each establishment was welcoming and thoroughly explained their passion to us. Our first stop was Foundation Brewery. I don’t like beer, truly, but I really enjoyed two of the three beers I tasted. Plus, when one of them, Pale Blue Dot, which was created to celebrate Earth Day and to support the local Sebago Clean Waters project, I was sold.

Our second stop was at Eighteen Twenty winery, whose owner Amanda explained how her love of wine drove her to make it out of something that grows well in Maine: rhubarb. She had me in stitches explaining how she got to the point of actually selling her craft, and I have to admit, rhubarb wine might be better than actual wine JUST SAYING.

Our last stop was at Hardshore Distillery for my poison of choice: gin. Founder Jordan showed off his incredibly cool copper distilling beast and explained every effort he and his team puts into making their smooth-as-silk gin.

HoneyMaker Mead, Portland | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Maine Mead Works: I also had to check out Maine Mead Works, because (and this is true) it sounded bada$$. Who else pictures Vikings and Lord of the Rings when you think if mead? Well, think again, because this place is classy! I suggest trying the tasting flight, which is based on the bottles they have in season.

Mead is made through the fermentation of honey, water and any other flavours you wish to mix in. The Honeymaker Mead at Maine Mead Works is made through the South African method, which is apparently different than what you would think mead would be. PS: Try the Lavender Mead. It’s the first alcohol I’ve EVER brought home from a trip, so that explains how great it is.

Where to eat

Highroller Lobster Co | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

High Roller Lobster Co: What started with two dudes and a food truck, turned into this trendy spot in the heart of Portland’s downtown. High Roller Lobster Co is just one of the man places to get a classic lobster roll, but did you know you can also get a lobster grilled cheese, lobster taco and a lobster on a stick? Yup. All right here.

Day four: Explore Old Port

After *buzzing* into town yesterday (ha get it?), you’re going to want to spend your second day in Portland (and fourth on the New England road trip) exploring Portland’s old port and historic district.

What to see

Portland Harbor Fish Market | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Harbor Fish Market: You’ll find the freshest fish and seafood right in the heart of the Portland waterfront at the Harbor Fish Market. See where many of the city’s restaurants get their catch of the day at one of the oldest fish markets on the east coast. Don’t worry; they won’t throw their fish at you!

Old Port: In Portland’s old port, you’ll still find cobblestones and red brick buildings paying homage to this old New England city. Wander the street and take a peek into the several one-of-a-kind shops. Make sure to stroll along Fore Street and Wharf Street and don’t miss the Longfellow street art. Henry Wadsworth Longfellow was a poet from Portland who is known for his poems capturing the plight of the Acadians.  

Portland Exchange Street | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Exchange Street: Where everything is happening in Portland. Seriously, from shops to restaurants, all the cool kids are hanging out on Exchange Street. Here is where you’ll find the infamous Holy Donut.

Portland Historic Waterfront District | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Historic Waterfront: Zigzag through the floating piers and watch the boats zoom by at the Historic Waterfront District. Here you’ll even find a piece of the Berlin Wall!

Congress Street: Find more of Portland’s history on Congress Street, including Congress Square Park, Public Market House and Monument Square. Keep your camera out because you’re going to want to keep snapping photos!

Where to eat

Becky's Diner, Portland | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Becky’s Diner: Go where the locals go to find the best eats in town. You’ll find that at Becky’s Diner on Commercial Street. Try the unbelievably delicious blueberry pancakes (made with Maine blueberries) or the lobster and Swiss omelette! PS: As a Canadian, I have to tell you, don’t you dare skimp on the real maple syrup.

The Holy Donut: Find out what all the fuss is about at the Holy Donut. These fresh and delicious doughnuts are made from Maine potatoes. Yup, that’s right potatoes. And you’re not going to have just one. There’s almost always a line up out the door so be patient, because they are freaking worth it.

Portland Lobster Co: Ready for lobster roll round two? The Portland Lobster Co was voted the best lobster roll four years in a row. Plus they have a great location right on the water with a picnic-style area that can’t be beaten. Go try it for yourself!

Day five: Munjoy Hill, Eastern Promenade and Portland lighthouses

Now that you’ve spent a day wandering around the Old Port, on day five of a New England road trip, it’s time to get out of the downtown and see some of Portland’s other famous areas.

What to see

View of Portland from Munjoy Hill | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage  #Boston #Portland #Maine #travel

Munjoy Hill: Like Boston’s Beacon Hill, Munjoy Hill is a historic residential neighbourhood. Many of the old ship captains’ homes still stand facing the water like guards of their own. Technically starting at Washington Street and then surrounded by water on three sides, Munjoy Hill is one of the more affluent neighbourhoods in Portland. Like Beacon Hill, it wasn’t always that way. Today you’ll find a quiet area with beautiful views everywhere you look.

Portland Observatory: While the Portland Observatory looks very much like a lighthouse, it is not a lighthouse. Built in 1807 by Captain Lemuel Moody, the 26-metre tall structure was used as a marine signal tower for passing ships. Today you can climb the 103 steps to the top to get a wonderful view over Portland and the surrounding bay. Keep in mind that the observatory is only open from Memorial Day (late May) to mid-October and costs $10.

Sumner Park: For a free view of the city, and a great place to catch the sunset, head to the highest point on Munjoy Hill located at Sumner Park.

Eastern Promenade: The Eastern Promenade is a massive park that stretches along the Portland peninsula’s most eastern side. Here you can take a walk along the trails, or lounge on the beach and stick your feet in the ocean. The most southern point is Fort Allen Park, where you’ll find monuments to several wars in American history.

Portland Head Lighthouse | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Portland Head Lighthouse: Next, head all the way to Cape Elizabeth south of Portland to visit one of the most famous lighthouses in the world: Portland Head Lighthouse. It’s also the oldest lighthouse in Maine.

George Washington commissioned the lighthouse before he became the first president of the US. The Portland Head Lighthouse is located within Fort Williams Park, which was operating as a military fort from the late 1800s until the mid-1960s. You can explore the old batteries that dot the coastline. New in 2019, out-of-town visitors will now have to pay $2/hour for parking within the Fort Williams Park.

Spring Point Lighthouse, Portland | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage  #Boston #Portland #Maine #travel

Spring Point Ledge Lighthouse: Heading north, you’ll visit Spring Point Ledge Lighthouse, a short, squat lighthouse with a small, rocky path jutting out from the shore. It dates back to 1897, but today you can tour the lighthouse and Fort Preble, where it is located. It is adjacent to the Southern Maine Community College.

Bug Light, Portland | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Bug Light: Also known as the Portland Breakwater Light, Bug Light is a tiny lighthouse located in South Portland. What’s interesting about this lighthouse are the fake Corinthian columns that decorate the side, are actually used to hide the seams of the iron façade. The land surrounding Bug Light has an interesting tale. During the Second World War, the area was used for a shipyard for the New England Shipping Company, where the crews, of mostly women, built 236 Liberty Ships, a military-grade cargo ship, for the war efforts. You can see a reconstruction of a hull’s frame at the park today.

Disclosure: I was invited on a tour with the Real Portland Tour through the Women in Travel Summit conference. All opinions are my own.

Real Portland Tour: Did you know that Portland burned to the ground, not once but four times in its history? I sure didn’t. That’s just one of the insane facts I learned from local Derek of Real Portland Tour. The 90-minute tour takes you along old roads of Portland and to the three lighthouses mentioned above. Along the way, Derek explains the city’s fascinating history and might even do a Portland rap for you! I highly suggest this knowledgeable and entertaining tour if you have limited time in Portland.

Where to eat

Bite into Maine: As the name suggests, you’re going to bite into Maine cuisine at this food truck located at Fort Williams near the Portland Head Lighthouse. Owner Sarah has concocted several versions of the classic lobster roll. Each at mouthwatering as the other. I tried the classic Maine style with Maine-made root beer and finished it off with a delicious blueberry whoopie pie. Dare I say it, I think this way my favourite lobster roll to date.

Duckfat Friteshack | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Duckfat Friteshack: Just writing about these delicious fries from Duckfat is making me drool. Duckfat makes their fries the Belgian way – double fried – but in duck fat, instead of oil. They were crispy, melt in your mouth, delicious. They also have a restaurant located in the Old Port, if you want more of a sit-down dinner.

Eventide: Get fresh oysters, a warm lobster roll and other tapas-style dishes at Eventide. This trendy spot serves up some delicious food. And I have to say, I really enjoyed the warm, buttery lobster roll. It’s different than anywhere else I tried.  

Where to stay in Portland, Maine

Budget – Black Elephant Hostel: This independently-run hostel is the only hostel operating in Portland. It’s definitely a funky place to stay just outside of the Old Port area in Portland. They have twelve different rooms that can accommodate a range of people.

Midrange – the Spring Point Inn: Run by the hospitality students at Southern Maine Community College, the Spring Point Inn is a lovely place to rest your head for the night. There are eight cozy rooms, with many overlooking the Spring Point Ledge Lighthouse. While the Inn is located outside of the city of Portland, it’s a comfortable place to stay in the mid-price range.

*Disclosure: I was hosted by Portland Harbor Hotel for a night. All opinions are my own.

Portland Harbor Hotel | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Luxury – Portland Harbor Hotel: If you want to feel treated like a queen right in the heart of Portland, then stay at the Portland Harbor Hotel. This lovely old hotel is Portland’s only AAA four-diamond hotel. The recent renovation gives the entire hotel a nautical theme, perfect for this east coast location. The service from when you check in to the thoughtful turndown service was exemplary. I could have stayed here in luxury forever.

One night on Maine’s Mid-Coast

Next up on the New England road trip itinerary is Maine’s Mid-Coast. Once you’ve got a taste of Maine’s most populous city, then you’re going to head north for the perfect place to relax and see the spectacular rugged coast.

Day six: Route 1 to Camden

You’re officially halfway on your New England road trip itinerary, but the best is yet to come. Start your morning with a coffee (see suggestions below) and hit the road!

What to see

Eartha at Garmin in Yarmouth, Maine | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Eartha Globe, Yarmouth: First stop is to visit Eartha, a giant, moving globe located at Garmin’s Maine office in Yarmouth. In fact, it’s the world’s largest revolving globe. As an avid traveller, I just had to check it out. It was built inside an atrium in 1998 at the DeLorme headquarters; Garmin bought the company in 2016.

L.L. Bean flagship and giant boot, Freeport: When you’re on a road trip, you have to check out giant roadside attractions. And the L.L. Bean boot is one of them. Located at L.L. Bean’s flagship store and outlet in Freeport, the giant boot and the surrounding shopping complex is a must experience. It’s the first and largest L.L. Bean store in the world and its open 24/7!

Androscoggin Swinging Bridge | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage travel blog #Boston #Portland #Maine #travel

Androscoggin Swinging Bridge, Brunswick: The Androscoggin Swinging Bridge is a pedestrian suspension bridge that crosses the Androscoggin River in Brunswick. Stop here for a little rest or stroll along the Riverwalk, because this is where you’ll hook onto the Scenic Route 1 for the rest of the trip.

Whaleback Shell Midden State Historic Site, Damariscotta: The Damariscotta River is known for its oysters, who love the cold, deep water. This place has been a gathering point for Indigenous Peoples for millennia before settlers arrived in the Americas. Evidence of this is at Whaleback Shell Midden State Historic Site, where heaps of oyster shells, discarded by the Indigenous peoples, were found.

Pemaquid Lighthouse, Maine | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Pemaquid Point Lighthouse, Pemaquid Point: This lighthouse is located at the southern point of one of the peninsulas along Maine’s coast. It was built way back in 1827 on the orders of US President John Quincy Adams. What’s neat about this lighthouse is where it’s located. The geological surroundings are striking, and the rocks look like they are folding into each other and the sea. Try to spot some of the sparkly white rock running like ribbons along the darker grey rock. PS, I totally called this place “Permasquid” like a squid with a perm, but it’s called Pemaquid.

Owls Head Lighthouse | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Owls Head Lighthouse, Rockland: Next stop is Owls Head Lighthouse near Rockland. Here, you’ll find a short lighthouse atop a hill. You’ll need to climb a few stairs, but the view is worth it. This little light overlooks the Penobscot Bay; you’ll just want to stare out into the sea forever.

Center for Maine Contemporary Art, Rockland: Take a break at the Centre for Maine Contemporary Art, located in Rockland. This art gallery is right in the heart of Rockland’s downtown, and perfect to stretch your legs and engage your mind. It’s open from 10am to 5pm, Wednesday to Saturday and noon to 5pm on Sunday. Admission is $8.

Rockland Breakwater Lighthouse | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Rockland Harbor Breakwater Lighthouse, Rockland: For your last lighthouse of the day, don’t miss the Rockland Breakwater Harbor Lighthouse. Located just outside the town of Rockland, this cottage style lighthouse sits at the end of a 1.4 km (7/8 mile) breakwater. You can walk the entire length and get up close to the building. We timed ourselves. It takes 18 minutes to walk along the rocky outcrop. I suggest not doing this during bad weather, or you’ll be swept into the ocean.

Megunticook Falls, Camden: The Megunticook River runs right underneath the town of Camden, so when you get here you have to check out the Megunticook Falls, a cascade of water that runs right from underneath the stores and into the harbour. Make sure to go on both sides of the falls for different views!  

Downtown Camden: Camden is known as the Jewel of Maine, and it’s easy to see why, with its tree-lined streets, homey-atmosphere, and lovely ocean views. Stroll along the downtown and duck into one of the many antique shops. And don’t forget to search for a bite to eat!

Where to eat

Higher Grounds Coffee, Portland | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage  #Boston #Portland #Maine #travel

Higher Grounds, Portland: Start your morning in Portland at Higher Grounds for coffee. They serve locally-roasted coffee and a variety of fine foods. Try their morning bun; it’s delicious!

Shuck Station Raw Bar, Newcastle: The Damariscotta River is known for the high-quality oysters that grow here. The cold, deep river is the perfect breeding ground for these delicious delicacies, so what better place to have your oysters and a shuck shack right on the river? Shuck Station Raw Bar does just that, plus they have a variety, depending on your tastes.

Sea Dog Brewing Co, Camden: Eat and drink your heart out at the Camden location of Sea Dog Brewing Co. From seafood to tacos to salads and burgers, they’ve got just about everything here. Plus you can sample their 10 different beers. Bottoms up!

Where to Stay on Maine’s Mid-Coast

Budget – Towne Motel: Located inside the town limits, this motel is a simple, yet affordable option for resting your head in Camden. The rooms are nautical themed to keep the with Maine coast vibe.

Midrange – The Inn at Camden Place: This Inn is located right on the Megunticook River in an old renovated factory. You’ll want to cozy up in their plush beds or sit at a chair by the window watching the river speed by.

Luxury – Grand Harbor Inn: This AAA four-diamond hotel is right in the heart of Camden, with views overlooking the harbour. Plus, this boutique hotel is pet-friendly, who can say no to that?!

Bar Harbor/ Acadia National Park (2 nights)

Cadillac Mountain Acadia National Park | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

You’re at the home stretch of the New England road trip itinerary. Spend the next two nights in Bar Harbor, right on the outskirts of Acadia National Park. On this leg of the trip, you’ll get up early for sunrise on Cadillac Mountain, wander the streets of Bar Harbor and walk along the rugged coast of Acadia National Park.

Day seven: route 1 to Bar Harbor

On day seven of the New England road trip itinerary, you’ll be taking Scenic Route 1 then leaving the highway to drive to Bar Harbor, a sleepy town in the offseason and a busy town in the summer and fall. That’s because Bar Harbor is the largest town next to Acadia National Park, where people flock to in the summer and go leaf peeping in the fall. But before you get there, you’ll want to stop at a few places first.

What to see

Main Street, Belfast: Like many small towns in America, Belfast has a beautiful and historic downtown. Take a quick stroll along the shops to see if anything catches your eye. Make sure to see the Belfast and Area Chamber of Commerce, which is situated in an old-timey gas station. Definitely one of the more colourful buildings in town.

Belfast heritage building, Maine | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Belfast Harbor Walk, Belfast: Hop onto the harbour walk path, which takes you through the Front Street Ship Yard where you can see some BIG boats in BIG slings being worked on.

Belfast Armistice Bridge, Belfast: You’ll take the path all the way until you reach the footbridge. The Belfast Armistice Bridge is a pedestrian bridge that crosses the Passagassawakeag River. It used to be an old rail line but was converted into a trail recently. Check out the River views from here.

Fort Knox, Penobscot: Next stop is Fort Knox! No, not that famous Fort Knox, which houses the US gold reserves. This is the other Fort Knox. It’s one of the best preserved military fortifications from the 1800s on the east coast. It was designed and built after the war of 1812, to protect the area from further British invasion. The troops here never saw military action. Today, the fort is open from May 1 to October 31. It costs $6 to enter, or $8 if you would like to visit both the fort and the observatory.

Penobscot Bridge and For Knox, Maine | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Penobscot Narrows Bridge and Observatory, Penobscot: The Penobscot Narrows Bridge is fairly new. It opened in 2006 as a replacement for the historic Waldo-Hancock Bridge that had corroded beyond repair. However, when building this bridge, the designers thought an observatory at the top of one of the support towers would be a cool idea. They were right. Today, you can take an elevator to the top of the word largest bridge observatories for views up and down the Penobscot River. You can get an $8 ticket that includes both Fort Knox and the observatory.

If you would like a free view of Fort Knox and Penobscot Bridge, then head across the river to Bucksport Veterans Park, in Bucksport, which is what I did since the observatory was not open at the time of my visit.

Main Street, Bar Harbor: You finally made it to Bar Harbor. Your first stop is to explore Main Street and surrounding downtown. Make sure to stop into any one of the unique shops along the downtown to get made in Maine products and souvenirs. Check out the Village Green and grab an ice cream at one of the delicious ice cream shops downtown.

Bar Harbor, Maine | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

West Street, Bar Harbor: Next head to West Street, which is the street nearest the harbour. This is where you’ll catch a boat tour if you elect to take one. You’ll want to take pictures at Agamont Park since it has such nice views over the surrounding bay. You’ll also want to come back here for dinner!

The Shore Path, Bar Harbor: For a quick walk, this 1.6 km (1 mile) round trip path follows along Bar Harbor’s sea wall. It passes by some of Bar Harbor’s most luxurious estates and gives excellent views of the surrounding bay and islands.

Sunset at Blue Hill Overlook: Make sure to check the time of the sunset when you go, because you’re going to want to take the drive up to Blue Hill Overlook for sunset. Because Blue Hill Overlook faces west, you’ll be in for a treat when the sun dips below the horizon. If you can’t get there for sunset, no worries, Blue Hill Overlook is still beautiful at other times of the day and should not be missed!

Where to eat

Bagel Café, Camden: Grab your fill of coffee and fresh bagels at the Bagel Café. Pick up two for the road! You never know when you might want a delicious snack!

West Street Café, Bar Harbor: Less of a café, more of a bistro, the West Street Café is a great spot to satisfy your hunger at dinner time. Try their lobster roll while you stare out their big windows to the sea!

Day eight: Sunrise and Park Loop Road

On day eight of the New England road trip itinerary, you’ll want to get up early for sunrise. Trust me; it’s worth it. Then, power through so you can explore the rest of Acadia National Park.

What to see

Acadia National Park at Sunrise | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Sunrise at Cadillac Mountain: Up and at ‘em! It’s time for sunrise on Cadillac Mountain. Timing is everything. It takes about 30ish minutes to get from Bar Harbor to the top of Cadillac Mountain (don’t worry you can drive right to the top), which means you’ll want to time your trip to arrive about 30 minutes before sunrise since that’s when the colours are at their best.

Did you know? Cadillac Mountain is the supposedly first spot in Maine and the continental US to see the sunrise. While the exact place may be up for debate, the height of Cadillac Mountain and the beauty of the surrounding area certainly leads people to flock here every morning for a beautiful sunrise. Just bring warm clothes and a couple of blankets, because it can get pretty windy up there.

Blue Hill Overlook: If you didn’t get a chance to catch sunset last night, then drive over to Blue Hill Overlook to take in the beautiful surroundings with the sun at your back.

Duck Brook Bridge: Before jumping onto the Park Loop Road, take a small detour to see the Duck Brook Bridge, which is part of the dozens of carriage roads that wind throughout Acadia National Park. And who can pass up a quaint little waterfall?

Thunder hole, Acadia National Park | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Thunder Hole: Jump onto the Park Loop Road 43km (27-mile) loop around Acadia National Park’s most beautiful scenery. Much of the trip is one way, so make sure to stop at every place you want to stop, because you won’t be able to turn around. Because it’s one way, you can actually park on the right side of the road, which the left lane can keep traffic moving.

Stop at Egg Rock Overlook, Schooner Head Overlook, and Great Head for a quick hike, then make your way to Thunder Hole for high tide. A naturally forming cave lies beneath the rocky surface. At low tide, you can head down the step to have a peek inside, but at high tide, it’s a different story. The waves and the cave combine to create a thunderous boom, giving the place its name. Apparently, the best time to go is between low and high tide, where the waves are just right to make the thunderous boom and launch the spray nearly 40 feet into the air. It’s a natural marvel you don’t want to miss!

Otter Cliff Overlook | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Otter Cliff Lookout: Another great scenic lookout stop is at Otter Cliff Lookout, located just a little further down from Thunder Hole. You can park in a small parking lot just off the road then make your way across the road to the overlook. Here you’ll get some amazing views of Acadia National Park’s rocky coast. I loved listening to the waves crash against the cliffs.

Little Hunters Beach: Next stop along the Park Loop Road is Little Hunters Beach. You can park in a small pull over and climb down the stairs to a beach that is hidden from view from the road. First, marvel at the little waterfall running right under the road. The beach is made up of smooth rounded rocks, created by erosion from the constant waves. You can hear the rocks scrape against each other as the waves roll back into the sea. It sounds like one of those rain sticks people had when I was a kid.

Jordan Pond, Acadia National Park | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Jordan Pond: After stopping at Little Hunters Beach, the Park Loop Road heads back inland, cutting a path through the middle of the park. Pull over at the Jordan Pond parking lot and head down to walk along the shore of this lake. The two lumpy mountains to the north are the Bubbles, after their round shape.

Where to eat

A Slice of Eden, Bar Harbor: Just like the name suggests, a Slice of Eden is a delicious spot for heavenly food. They have everything from sandwiches to salads to breakfast foods to cakes and treats. You’ve got to try their whoopie pie, which is Maine’s official state treat (their official state dessert is blueberry pie.) For the whole story on that, you have to ask Derek of the Real Portland Tour!

Whoopie Pie in Bar Harbor, Maine | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Project Social, Bar Harbor: If you want a light lunch or dinner, or can’t decide what you want, then Project Social is where it’s at. This place is known for its tapas and craft cocktails.

Thirsty Whale, Bar Harbor: For pub fare and a spot that was recommended to me, head to the Thirsty Whale, a charming tavern in the heart of Bar Harbor. They’re known for their lobster rolls, fish sandwiches and homemade chowders. Definitely worth a stop!

Day nine: Western portion of Mt. Desert Island, back to Portland

It’s your last day on the New England road trip itinerary! I know, so sad, I bet the trip just flew by. After checking out a few places on the western side of Mount Desert Island, you can take the I-95 to rush back to Portland. If you’re trying to make it back to Boston, there’s the last Downeaster that leaves Portland at 6:15pm and arrives in Boston for 8:45pm. If you’re not rushing back, then take it easy and enjoy the rest of your trip!

What to see

Bass Harbor Lighthouse | This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

Bass Harbor Head Lighthouse, Bass Harbor: In the western portion of Mount Desert Island, which is where the majority of Acadia National Park is located, you’ll find the Bass Harbor Head Lighthouse. This is also the southernmost point of the island. A Coast Guard family occupies the house next to the light, so respect their privacy, but you can get up close to the lighthouse and the original fog bell. Take the short Bass Harbor Lighthouse Trail to get some incredible views of the ocean, the red Acadia National Park rocks and the lighthouse all on one photo!

Wonderland Trail: If you want to take a short, easy hike while in Acadia National Park, then the Wonderland Trail is the perfect place to do that. This 2.5km (1.6-mile) trek is an easy in-and-out trail that takes you through forest before spitting you out on the rocky shoreline.

Where to eat

Choco-Latte, Bar Harbor: Fuel up your morning at Choco-Latte in downtown Bar Harbor. They have a lot of items made with fine chocolates, but you can also get breakfast food and sandwiches too. You have to try their chocolate latte! It’s delicious.

Where to Stay in Acadia National Park

Budget – Quality Inn: This motel may have budget prices in Bar Harbor, but the digs are not. It was a cozy and comfortable stay, and the motel is just on the outskirts of town. It was the perfect medium between a short jaunt into town and access to the park. One morning, three deer decided to visit on the hill right behind the motel, a perfect little slice of nature, right in their backyard.

Midrange – Acadia Hotel: In the centre of Bar Harbor sits the Acadia Hotel, a friendly and comfortable boutique hotel with a winning location. You’ll enjoy the nautical themed rooms that are beautifully decorated. Plus Project Social is part of the hotel, so you don’t have to go far for a great bite to eat.

Luxury – Bar Harbor Inn: If you want to stay in luxury, then you’ll find it waiting for you at Bar Harbor Inn, a historic waterfront hotel. From their plush rooms to the stunning views of the ocean, this place can’t be beaten. They also have a water view infinity pool!

New England Road Trip Itinerary

From Boston to Bar Harbor, this New England road trip will take you to the best of the best along the coast. Visit historic downtown Boston, stroll the trendy Portland streets, take in the beautiful scenery along Maine’s Mid Coast, and finally enjoy some time outdoors at Acadia National Park.


Inspired? Pin it:

This New England road trip itinerary will take you on the scenic route from Boston to Portland, Mid Coast Maine and Acadia National Park. | My Wandering Voyage #Boston #Portland #Maine #travel

You Might Also Like

2 Comments

  • Reply Julie July 21, 2019 at 9:05 pm

    I love road trips and this looks like a great one – so much attention to detail! We were in Acadia last summer. I’d love to go back and do this sort of trip to get there.

  • Reply Katie Minahan July 21, 2019 at 9:05 pm

    This is so incredibly thorough. I’ve never been to Boston or Maine and this sounds like such a great way to see what both destinations have to offer.. dreaming of lobster rolls now…

  • Leave a Reply

    This site uses Akismet to reduce spam. Learn how your comment data is processed.