From Boston to Maine: The Ultimate 3-Day New England Road Trip Itinerary

Take a New England road trip and drive from Boston to Portland Maine for a weekend in the summer. Discover places to visit in Maine when you travel from Boston to Maine by Car. Find out about fun things to do in Portland in summer.

A business trip to Massachusetts followed by a commitment in Chicago meant that we had a long weekend at our leisure. My motto is Work to Live, Live to Travel, Travel for Work, so the idea of making this a bleisure trip was a no-brainer. 

What better way to spend an August weekend than driving from Boston to Portland Maine in the summer. 

While Maine getaways are often deferred to the Fall in order to see spectacular foliage, summer in Maine is really a lovely time to visit. 

On this 3 day New England road trip itinerary, we'll explore places to visit in Maine and beyond. Read on for ideas of how to explore Boston to Maine by car.

Boston to Portland Maine Road Trip Map

Click on the image of the map below to open an interactive version in Google Maps with information on the drive from Boston to Portland, Maine (and beyond) and Maine getaway points of interest.

New England Road Trip Stop #1: Newburyport Massachusetts

We started our road trip from Boston to Maine with a visit to Newburyport, Massachusetts. Located about 35 miles outside of Boston, Newburyport is a great place to stop, stretch your legs, and grab a coffee. 

Newburyport is older than the United States itself and was home of the first "Tea Party" rebellion to fight the British Tea Tax in the American colonies. Steep in the atmosphere of this quaint port town filled with colonial brick buildings. 

I especially loved the doors on Unicorn Street. In fact, I loved that Newburyport, this distinguished little historic gem had a Unicorn Street. Such a whimsical name. Allow about an hour to give yourself a quick overview of Newburyport.

New England Road Trip Stop #2: Portsmouth, New Hampshire

We had a think about where to visit in New Hampshire as we plotted our itinerary and settled on Portsmouth. New Hampshire was our second of three states covered in a single day on this New England road trip. If you have more time for this Boston to Maine drive than we did, consider spending a night in Portsmouth. 

Alas, we only had a couple hours and spent the time admiring the spire in the town center, historic architecture, and local shops. We enjoyed a a lovely soft ginger and raisin "hermit" in Portsmouth from Ceres Bakery. Make sure to stop in for a treat. 

I felt oddly at home in Portsmouth. I think it was due to the ornate Georgian doors dotted about town that reminded me of where we live in Dublin Ireland.

(1) Bank in Newburyport, MA
(2) Unicorn Street in Newburyport
(3) Church spire in Portsmouth, NH
(4) Ginger and raisin "hermit" from Ceres Bakery.

New England Road Trip Stop #3: Kittery, Maine and Around

We finally crossed over into Maine and made a stop in Kittery, the oldest place in Maine (settled in 1623). We loved the savory sunflower and Gouda scones, sweet/savory crueller and coffee at Lil's.

Just outside Kittery, we made a fascinating historical stop at Fort McClary, a defensive fortification that dates back to the early 1800s. Fort McClary cost $4 per person paid by the honor system into a sort of mailbox by the entrance. Fort McClary features two things: great sea views and local Revolutionary War history.

(1) Ducks near Fort McClary
(2) Fort McClary
(3) Lil's Cafe in Kittery, Maine

We also paid a visit to Cape Neddick Nubble Lighthouse. Maine can get quite crowded with folks decamping from Boston and other cities for the weekend. We ran into some traffic near Nubble Lighthouse and had a little bit of trouble finding parking. Stick with it though. 

While some people stop here for a picnic, others pop-in for sea views and a photo and are done in about 15 minutes. Our patience paid off and we were able to park in the end for a short stop to stretch our legs and enjoy the view.

SIDEWALK SAFARI SPOTLIGHT: If you like lighthouses, consider making a visit to Westfield NY if you find yourself near Buffalo. The Barcelona Lighthouse sits on Lake Erie and you may even find a vulture perched on top!

Overall, we had a great time today driving from Boston to Portland Maine. The only "miss" was the Wiggly Bridge. We couldn't stop because there was no legitimate parking in the vicinity and stern warnings about simply pulling over at the side of the road. 

We also wish we'd had more time to investigate things to do in Ogunquit, Maine which is located between Kittery and our next stop, Wells.

New England Road Trip Stop #4: Lunch in Wells, Maine

We continued our drive from Boston to Maine and stopped for a bowl of clam chowder plus lobster roll shared for lunch at Billy's Chowder House in Wells, Maine. That day I learned that the lobster in a Maine lobster roll is cold! 

The lobster roll paired well with a Hidden Cove Blueberry Ale served with fresh Maine Blueberries. Of course, make sure to designate the next driver to make sure there are no issues with the next leg of the drive.

(1) Hidden Cove Blueberry Ale 

(2) Billy's Chowder House 

(3) Lobsters in Kennebunkport 

(4) Cape Neddick Nubble Lighthouse

New England Road Trip Stop #5: Kennebunkport, Main

Kennebunkport came to fame as the vacation getaway for both Presidents Bush. Kennebunkport is lovely if you can get beyond the horrible, horrible summer traffic. We had to circle the town twice before we managed to find a parking spot along a strip of shops. 

Kennebunkport has some lovely architectural accents like a golden sailing vessel atop a building in town but damn... the traffic in summer is problematic and pretty much ruined the experience for me.

(1) Welcome to Kennebunkport

(2) Bush compound at Walkers Point

We did manage to catch a glimpse of the Bush compound at Walkers Point. No Dubbyah sightings on our visit to Kennebunkport though aside from a photo of George W. Bush at a local lobster restaurant. There is a small parking lot with a scenic viewpoint that gives a nice view of the compound.

New England Road Trip Stop #6: Biddeford, Maine

We finished our Boston to Maine drive with a tasting paddle of Maine craft beer at Dirigo Beer. Serving the beers in a muffin pan was genius! I particularly liked the Champagne du Maine sour. 

We learned that just after our trip, Dirigo Beer closed down their tasting room. Still, the area is worth exploring for a fab urban renewal vibe and waterfall views. 

The old clock tower in Biddeford looks like it fell from somewhere. I would love to hear the story of how it came to be here.

(1) Spicy coconut fried chicken sandwich at Liquid Riot

(2) View from Dirigo Brewery in Biddesford, Maine

(3) Ruined clock town in Biddesford, Maine

(4) Weathervane in Kennebunkport

The Run of the Mill Public House and Brewery is another option in the area to consider now that Dirigo is no longer open.

New England Road Trip Stop #7: Portland, Maine

We parked the car in Portland Maine and spent the rest of the day at the end of our Boston to Maine road trip on foot. It's a good thing we ditched the car too. 

Portland is known for some amazing craft beer. We sipped a tasting flight of craft beer at Shipyard Brewing for just $6. 

After taking a short walk around Portland, we finished the day with craft beer and dinner on a comfy couch at Liquid Riot. A spicy coconut fried chicken sandwich with bacon and habanero orange sauce plus a cheese board went well with their Start Wearing Purple tart and fruity craft beer creation. 

Liquid Riot makes imaginative beers with unusual flavor combinations. Don't be shy about asking for a taster before committing to a pint.

Things to do in Portland Maine 

We spend the next day of our New England road trip exploring all the cool things to do in and around Portland, Maine. 

Rwanda Bean

We literally stopped with brakes screeching when we saw "whoopie pies" in our rear view mirror. 

We stopped at Rwanda Bean twice during our time in Portland. On our first visit, we tried a cappuccino and two flavors of whoopie pies (traditional Maine-iac and the Bromance). 

We noticed that you could order a cold brew coffee flight after we'd ordered our cappuccino. We stopped back in to Rwanda Bean later in the day to try four different cold brews. I was definitely energized after the experience!

(1) Cold brew tasting paddle at Rwanda Bean in Portland

(2) Facade of Rwanda Bean advertising whoopie pies

Portland Head Lighthouse

Portland Head Lighthouse was just a 15 minute drive from where we were staying in Portland, Maine.

Portland Head Lighthouse was commissioned by George Washington, so needless to say, there is a lot of history here. 

The area around Portland Head Lighthouse offers dramatic views. Check out the lighthouse and then take a walk along the coast. 

We especially enjoyed both the colorful flowers and colorful butterflies in the Butterfly Garden near Portland Head Lighthouse.

(1) Butterflies at Portland Head Lighthouse

(2) Portland Head Lighthouse

(3) Whoopie pie from Rwanda Bean

The area around Portland is quite compact to explore. We took a drive and then a lovely hike at Maine Audubon Society's Gilsland Farm. 

It takes less than 30 minutes to get from Portland Head Lighthouse to Gilsland Farm by car if there is no traffic. Grab a trail map at the visitors center and get some fresh air and a walk. Gilsland Farm was a quiet place to take a relaxing walk. 

I suspect we needed to come much earlier in the morning to see more wildlife but on our afternoon visit we saw a couple birds of prey and a bunch of turkeys. Still a very cool place for a relaxing and not-too-strenuous hike.

SIDEWALK SAFARI SPOTLIGHT: Another great place to see turkeys in the wild is on a walk through Mount Auburn Cemetery in Boston.

Maine's Craft Beer Scene

As we've seen so far, Portland has a great reputation for craft beer. Pay a visit to Lone Pine Brewing Company on the outskirts of downtown Portland. If you don't have a designated driver, make sure to take an Uber or Lyft to get there. 

Lone Pine has a fantastic collaboration with Holy Donut. The Holy Donut Triple Berry IPA was fab; think of a hoppy sour. Did you know that Maine makes their donuts with mashed potatoes?

(1) Lone Pine Brewing Company tasting tray with Holy Donut samples

(2) Lone Pine taproom

(3) Good Fire Brewing Moon Jellies craft beer

(4) Craft beer taps at Shipyard Brewing in Portland Maine

You can walk from Lone Pine Brewing Company around the corner to Good Fire Brewing. De 'Nada empanadas onsite is a tad expensive ($5 for a tiny treat) but a delicious accompaniment to beer. 

Goodfire Brewing Moon Jellies craft beer really hit the spot. Back in Downtown Portland, try some kettle corn with a Preble Raspberry Sour from Fore River Brew at the Little Tap House. As they say:

"Beauty is in the eye of the beerholder"

Take a Lyft to Bissell Brothers Brewing Company. Industry Versus Inferiority is an IPA but light on the hops. We definitely enjoyed the Lux Rye Pale Ale at a table made out of old skateboards.

Our final craft beer experience in Portland had a very local feel. Bog So Hard from Sebago Brewing is made with 1300 lbs of Maine cranberries.

SIDEWALK SAFARI SPOTLIGHT: Looking for other great places in the U.S. to sample craft beer? Spend one day in Brooklyn and pay a visit to Brooklyn Brewery. Hang out in Cleveland for a day and have a drink at Great Lakes Brewing Company housed in a building where Al Capone himself used to drink. Visit Ann Arbor and take a detour to Corner Brewery in Ypsilanti. Get a taste of Buffalo including a craft beer flavored with Concord grapes. Plan a workcation in the Hudson River Valley or spend a weekend in Saratoga Springs and explore the craft breweries of Upstate New York.

Walk Portland

Portland, Maine is a small, compact city that you can walk from end to end. Check out Longfellow Books for some local authors and then wander around downtown. 

While our guide book recommended Longfellows Books in Portland, I preferred Sherman's Books and Stationary. I like to buy local authors and Sherman's Books has a Maine authors section and even a bargain Maine books section. 

When we visited, there was a summer craft fair happening. Shop and admire the classic architecture in Portland including that of the historic State Theatre.

Dinner at David's Restaurant

David's restaurant in Downtown Portland is a real treat. We enjoyed chowder and mussels to start followed by exotic mushroom ravioli and haddock with peekytoe crab and a blueberry sauce.

(1) L.L. Bean giant boot

(2) Holy Donut

(3) Local Authors at Sherman's Books and Stationery

(4) Art lighthouse in Portland Maine

Holy Donut

Who doesn't love doughnuts for breakfast?! We arrived at Holy Donut early and there was a line at 7:15 am on a Sunday. 

Not only does Holy Donut participate in beer collaborations with the likes of Lone Pine Brewery discussed above but they also make kick-ass potato-based doughnuts in imaginative flavors. We enjoyed the maple bacon glaze on a blueberry donut which went down well with Maine wild blueberry coffee.

New England Road Trip Stop #8: L.L. Bean Factory Store

Full of sugar and properly caffeinated, we embarked on the next leg of our Maine road trip. I unleashed my unbridled American side with a shopping extravaganza at the L.L. Bean factory store in Freeport, Maine. 

I grew up ordering from L.L. Bean and it was really cool to browse their flagship store. Plan to spend at least a few hours and a pretty penny shopping for sturdy, casual and adventure clothing.

New England Road Trip Stop #9: Bowdoin College and Around

We next set our sights on Bowdoin, Maine which is about a 20 minute drive from Freeport. We stopped to bounce our way across the Androscoggin Swinging Bridge in Topsham. At least this bridge has some limited parking unlike the Wiggly Bridge south of Portland.

(1) Ice cream at Island Candy Company

(2) Polar Bear at Bowdoin College

(3) Bowdoin College

(4) Bridge near Sea Dog Brewpub in Brunswick Maine

Stop for a lobster roll and calamari for lunch washed down with a peachy Sunfish craft beer at Sea Dog near Brunswick, Maine.

Stop in and take a wander through the Bowdoin College campus. It will be fairly quiet if you visit in summer and you'll find plenty of free parking on the weekends. We were especially impressed by the polar bear statue on the Bowdoin College campus.

New England Road Trip Stop #10: Maine Maritime Museum

The Maine Maritime Museum in Bath features a built-to-scale sculpture of Wyoming, a wooden six-masted schooner built on this very site. The lobster car was also pretty rad. A quick detour to the Maine Maritime Museum is a fun diversion.

(1) Sculpture of Wyoming at the Maine Maritime Museum

(2) Lobster car at the Maine Maritime Museum

(3) Sunset near Potts Point, Maine

(4) Estes Lobster House near Potts Point, Maine (now closed)

New England Road Trip Stop #11: Land's End

We based ourselves in Bath, Maine for one night, about 45 minutes outside of Portland. From Bath, we had a few options of where we might explore. 

We considered visiting the popular Boothbay Harbor but we were short on time and the traffic in summer is known to be nightmarish at a choke point in the road on the way from Bath which can sometimes back up for miles. 

Instead, we drove to Bailey Island and Land's End for a more relaxing road trip experience. We encountered very few cars and not that many people. Lands End features a small shop, a large statue of a lobster fisherman, and scenic rock formations looking out to sea.

SIDEWALK SAFARI SPOTLIGHT: Looking for other U.S. road trip ideas? Head south and take a drive between Naples and Tampa, Florida on a Florida Gulf Coast road trip. Take a Houston to Austin drive for a taste of Texas. Drive the California Coast for a seaside adventure filled with wine, wildlife, and views.

New England Road Trip Stop #12: Giant's Stairs Trail

The Giant's Stairs Trail on Bailey Island is a bit hard to find. We drove by the tiny road that leads to the trail twice without seeing it. Pro tip: Use and trust Google Maps navigation to guide you. You'll wonder: could it really be down this tiny residential road? Yes.

(1,2) Lands End
(3) Lobster fisherman at Lands End
(4) Potts Point

We took a short seaside walk and sat among the rocks at the Giant's Stairs on Bailey Island before continuing our drive. Definitely make time to stop here if you enjoy scenic views and fresh sea air.

New England Road Trip Stop #13: Island Candy Company

We stopped on a whim at Island Candy Company on Orr's Island. The Maine salted caramel ice cream was fab. Sit in the sun outside while you eat your frozen treat.

New England Road Trip Stop #14: Potts Point

The public road simply ends and you need to walk down a gravel road for about 10 minutes to get to Potts Point. Follow a narrow spit of land on foot and find yourself on a shell covered beach. Evening golden hour is a great time to visit Potts Point. We even saw some cute plovers.

As the sunset over Potts Point, we found our short Maine road trip coming to an end.

New England Road Trip Stop #15: Bath, Maine

After a restful evening at our bed and breakfast, we took a quick walk through Bath, Maine before heading to the Portland International Jetport (less than an hour away by car). 

There are some fun shops in downtown Bath including a shop that sells local crafts. My favorite part about Bath was exploring the residential streets. The white and pastel paints seem to dazzle in the sun. Local residents showed their American pride with U.S. flags flying outside or framing a doorway.

(1) Breakfast room at Benjamin F. Packard Bed and Breakfast

(2) French toast at Benjamin F. Packard Bed and Breakfast

(3) Bright yellow house in Bath, Maine

(4) American flag in a doorway in Bath, Maine

Where to Stay on a Boston to Maine Road Trip

After flying in to Boston's Logan Airport, we started our road trip with a few nights in Boston. The Fairfield Inn and Suites Boston Cambridge was a solid home base to explore Boston and had good driving access into and out of the city. 

In Portland, we stayed at the Residence Inn by Marriott. Warning: hotels in Portland in the summer can be extremely expensive. The Residence Inn would have been over $300 a night if we hadn't used some Marriott points. 

Portland is popular in the summer with limited hotel stock which contributes to the issue. We spent one relaxing night at the end of our trip at Benjamin F. Packard Bed and Breakfast in Bath, Maine. The house dates back to 1790 and is also home to two Bergamesco sheep dogs. I've never seen dogs with dreadlocks before! 

We enjoyed a great breakfast and evening port service. Our stay at Benjamin F. Packard House cost $179 plus tax.

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We took this trip in August 2019. This post was last updated in June 2023.