When an old college friend moved to Boston, I took the opportunity as an excuse to reconnect and explore an area of the east coast I hadn’t yet visited. This is the story of how a week-long Boston to Maine road trip became my canvas for crafting new memories and embracing the beauty of the open road.
The trip was the perfect blend of vibrant city life, rural adventure, and serenity at the sea. I couldn’t have anticipated the experiences, encounters, and breathtaking sites that awaited.
If you’re thinking of taking a Boston to Maine road trip, here’s a quick rundown of my trip itinerary and what I would do differently.
Day 1 of the Boston to Maine Road Trip: Hello, Boston!
Day 1 of my Boston to Maine road trip was primarily a travel day.
After 3.5 hours on the road, I braved through a symphony of honking horns, battled dead phone batteries, and faced a series of wrong turns. But, perseverance finally led myself to the tranquil streets of Boston’s Roxbury suburb, at last.
If you’re prone to travel anxiety on the road, beware: those Mass ‘Pike drivers are no joke!
Once I had settled in, said my “Hello’s”, and got a brief tour of my friend’s apartment, we got our CharlieCards and hopped on The Green Line of the “T” train into the old city center.
Upon arrival, my friend was my own personal guide as we walked to the city’s most iconic spots.
He pointed out sites like Fenway Park, Boston’s legendary baseball stadium and home of the Boston Red Sox, and the Freedom Trail, a historic walking path that connects sites that played a role in the American Revolution.
We also strolled through many of the city’s vibrant shopping sites nestled between its charming cobblestone streets. If you ever get the chance to see Faneuil Hall and Quincy Market, I promise, you won’t regret it!
We ended up grabbing a light dinner at Yard House just outside the Prudential Center Shopping Mall before ending the evening at Boston Commons, one of the oldest public parks in the United States.
In summer evenings, this area of Boston comes to life with softly illuminated pathways and street performers. It was a peaceful escape and a chance to appreciate the city’s beauty in a different light.
Day 2 of the Boston to Maine Road Trip: Salem & Sea
On the second day of my Boston to Maine road trip, I woke up early and took a brisk walk. This time, to Ula Cafe in the Jamaica Plain neighborhood of Boston. Baked goods, fresh coffee and artsy, outdoor vibes are always a good idea when the sun is beginning to rise.
My friend and I then explored his quiet neighborhood of Roxbury a bit, seeing Malcolm X Park, before heading back to the apartment and parting ways.
By mid-morning, I continued my road trip to Maine. I drove up the coast, taking I90 to back roads off of 1A, north of Boston Logan International Airport. This helped avoid some of the weekend city traffic on my way to Maine. Plus, then I could make a quick detour to the city of Salem and see the harbor.
An Afternoon in Salem, MA (approx. 4 hours)
In Salem, I first parked at the Riley Plaza West Lot and walked the brick-lined Essex Street Pedestrian Mall. I’m not much of a shopper and I didn’t have time for a proper tour, but the ambiance was nice. The city has a rich history of witch hunting and it was prominent in the names of the street’s many shops, like “The Magic Parlor” and “Wicked Good Books”.
From there, I wandered a bit more. I walked a large loop. Starting from the Central Wharf and harbor area, I made my way to the Salem Witch Museum, where I found myself staring at the House of the Seven Gables. I’m a sucker for unique art, so, seeing Herb Mackey’s Metal Sculpture Yard close by, I passed by there, too. It reminded me a bit of the Magic Gardens of Philadelphia.
All this walking built up an appetite, so, Ye Olde Pepper Companie candy store was next on the agenda. I did end up scoring something a bit more substantial back in town. But, that was well after I headed back to the Salem Maritime National Historic Site and the Derby Wharf Light Station, one of the first of many lighthouses I would see on this trip.
I ended my afternoon in Salem with a visit to the Salem Witch Village and Salem Witch Trials Memorial, where I eavesdropped on the last leg of a walking tour (hehe).
In hindsight, I wish I had spent more time visiting Salem, MA. The Peabody Essex’s Museum and Salem Pioneer Village are still on my to-visit list. I’ll definitely have to book another weekend trip or two. Perhaps, in the fall, when Halloween tourism picks up?
From Boston to Maine (Finally!)
However, I had already booked a night at family-run Moody’s Cottages in Wells, Maine, and still planned on stopping at Cape Neddick’s Nubble Light (York, ME) before then, so I had to get going. The room itself wasn’t anything too special, but I found its employees and location delightful. The beach was well within walking distance, so, you bet I ended my day there. (Contact directly for best rates and availability- [email protected]!)
Day 3 of the Boston to Maine Road Trip: Kennebunkport and Portland to Rockland
Day 3 of my Boston to Maine road trip was the last day I was traveling alone.
I planned on picking up my boyfriend from Portland International Jetport later in the day.
(There are many reasons why traveling with a new partner is NOT on my bucket list again, but, you can get to those later…)
For now, I could make my way up the coast of Maine at a leisurely pace.
My parents had traveled to Maine months prior and suggested to stop in the harbor town of Kennebunkport. So, I began the day there.
Kennebunkport, ME
Having a whole day to spare, I made my way to coastal Kennebunkport via the neighboring inland town, Kennebunk, Maine. Sure, it was the “long way”, but scenic views of the town’s boutique shops and Wedding Cake House (104 Summer St. Kennebunk, ME 04043) was worth the detour. The private and restored Victorian home, is famous for its detailed wood trim, reminiscent of icing on a wedding cake.
Once in Kennebunkport, I drove through some of the neighborhood streets. When traveling, I like to go off the beaten path to get a better sense of daily life in the areas I visit. Along Ocean Avenue, I dreamt of someday owning an ocean-front home as beautiful as those that lined the street.
Of course, that was before visiting Blowing Cave Park to get a glimpse at former President George H.W. Bush’s Walker’s Point summer home. That place is massive and so beautifully kept! The other homes easily paled in comparison.
One of the Bush daughters happened to be visiting the Walker’s Point home while I was in the area. Dozens of black SUVs and secret service cars lined the driveway.
A Quick Run-In With the Police
Had I known a bit more about the area, the Maine Classic Car Museum would have been a great next stop.
Instead, I back-tracked and pulled over in a small parking lot to look at a map (FYI, the Maine coast has poor Verizon cell service). Within 30-seconds, a policeman knocked on my car window asking me to leave the area. I was lucky I was in my vehicle, or else I would have been stuck with a parking ticket. Oops!
I ended up stopping at Drake’s Island Beach before finding my footing again.
The new plan for this leg of my Boston to Maine road trip? I’d go to the quiet Timber Point Trail (1.4mi loop), in Biddeford, Maine to walk along the water and see a historic home. From there, I would drive to Cape Elizabeth and see Portland Head Light before finally picking up dinner to-go. Oh, and my boyfriend. Whose flight to Portland was now unexpectedly delayed by 90 minutes. (You just have to roll with the challenges of travel as they come!)
We had hotel reservations for the night at Rockland Harbor Hotel. So, we still had a few hours’ worth of nighttime driving ahead of us.
Day 4 of the Boston to Maine Road Trip: Adventures in Acadia
This leg of the Maine road trip was my favorite.
Today was all about Acadia National Park, easily one of the best places to visit in Maine!
You can read all about how we spent an action-packed day seeing Acadia landmarks like Thunder Hole, Sand Beach and the Carriage House at the link above.
We settled into our room at the Bar Harbor Villager Motel before the sun set. Then, we made our way into Bar Harbor itself to enjoy a roof-top dinner at Bar Harbor Beer Works for tasty (and reasonably-priced) American cuisine. The pub was packed!
Day 5 of the Boston to Maine Road Trip: Adventures in Acadia
By this point, my Boston to Maine road trip was coming to a close.
To make the most of our remaining visit to Maine, my boyfriend and I dedicated the first half of the day to the Acadia sites we hadn’t gotten to the day before. Cadillac Mountain and Bass Harbor Head Light? We went, we saw, we conquered.
The second half of the day was spent driving south/west, so we wouldn’t have to spend ALL of the next day driving home.
We landed in the Durham, Maine area, where we booked the Fisher Ridge Yurt, through Airbnb for a unique stay.
I had never before stayed in a yurt, but found the overall experience to be a cozy form of “glamping”. Our accommodating hosts, a former Survivor contestant and his daughter, provided extra amenities like board games and firewood. Plus, the property itself had hiking trails. It even backed up to water, where guests could take out host-provided kayaks and canoes. Despite the lack of a fancy toilet, we had a great time and can’t wait to go back!
Our dinner in Lewiston, Maine, on the other hand was memorable for all the wrong reasons. It took a while to be seated in an empty restaurant, which should have been the first red flags. Then, when it came time to order, I asked for lobster bisque (when in Maine, right?) but was shot down by the waitress even though the menu said my main dish came with it. Afterwards, my boyfriend asked which soups they did have, and they actually gave the lobster bisque to him! I’m not totally sure what was going on there, but it created a funny travel story we look back on to this day.
What a way to end the trip!
Back to Boston & Beyond
If you’re wondering what to visit in Maine, or are planning a Boston to Maine road trip yourself, I recommend checking out a few of the key sights in this trip itinerary.
From the spooky city streets of Salem, Massachusetts to the serene coastal views of Wells and Kennebunkport, to the mountaintop adventures waiting to be had in the national park of Acadia, a road trip from Boston to Maine has plenty to offer.
But, don’t be afraid to go off course and plan your own route. Spontaneous trips can be just as fun and worthwhile!
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