Pack your bags, folks, because we’re going on a whirlwind trip through New England where clam chowder reigns supreme, the fall foliage is like a postcard, and yes, I drove a Duck Boat (everyone survived!). From Harvard to Bar Harbor, here’s the lowdown on our quirky, charming, and occasionally drafty adventures.
Day 1: Harvard – Cheeseburgers & Gilmore Girls Vibes
Why did we start in Harvard? Because we could! Our first stop was Charlie’s, a classic diner straight out of 1951 (really it was opened in 1951 and I don’t think it has been updated much since), where cheeseburgers and fries were the order of the day. Sure, we could’ve gone intellectual with a quiche or something, but when in college-town…
Then coffee and it was off to the Harvard Book Store, which felt like walking onto the Gilmore Girls set. Books, souvenirs, and just the right dose of “I could be Rory Gilmore, right?”
Dinner was a highlight at the Bostonia Public House where I, a non-clam fan, was seduced by the most delightful clam chowder. We capped the night with live Irish music and maybe (definitely) a pint at a cozy Irish pub with some real Irish music. Cheers to day one!
Day 2: Duck Boats & Brownstones
Morning coffee at a quirky art-filled café was the perfect start. Then came the moment of truth: the Boston Duck Boats. These amphibious rides are a must, but the real thrill? I drove one. Yes, me, behind the wheel, on the Charles River, and no collisions—thank you very much.
We explored Boston’s famous brownstones, which are everything Instagram dreams are made of especially with the pumpkins and lettuces. But beware when your airbnb says the phrase “Paid Parking” as it apparently means you pay, even after you’ve parked. Lesson learned. Parking is not included.
Lunch at The Paramount was deliciously low-key, and we rounded off the day with history at the Union Oyster House and the bench from Good Will Hunting. “How ’bout them apples?”
Anniversary Lobster & Cheers to Cheers
Did I mention it was our anniversary? We celebrated in style at a hidden, fancy restaurant that served lobster gnocchi so good, we ordered seconds. Curt dabbled in steak tartare, while I focused on swooning over every bite.
Naturally, no Boston trip is complete without a visit to Cheers. Yes, it’s touristy. Yes, it’s worth it if not just to check it off the “must see” tourist list.
Vermont: Flannel, Foliage & Farm-to-Table
From Boston, we hit the road to Vermont, aka Fall Wonderland. Route ? (because I forgot) treated us to postcard-perfect views of covered bridges and barns framed by fiery autumn colors.
Woodstock, VT stole our hearts. Lunch at SANTE was a masterpiece of local ingredients—BLTs made with Vermont bacon, cheddar apple salad with cider vinaigrette, and fried chicken that dreams are made of. We chatted with the chef/owner about his farm just outside of town. So it’s legit!
We popped into the Vermont Flannel Company, but alas, flannel dreams were dashed as they were out of my size. Maybe one day…
A surprise highlight? A maple farm visit! Who knew there were flavors of maple syrup? My life is forever changed. We loved learning of the process to making the golden syrup. Here all this time I thought it came straight from the tree to the bottle. It’s a whole process! We snapped up a few bottles and headed on our way to Kennebunkport.
We stayed in a cozy bed and breakfast called the Snowed Inn in a tiny ski town called Killington. The owners/host were so sweet and kind and the fresh breakfast was delicious!
Kennebunkport: Coffee & Bushes
Onward to Maine, first stop was to grab a lobster roll at a place called Mabel’s that had a plethora of photos of George HW Bush on the walls. Apparently this was his favorite hangout! I didn’t even know that he lived there! We even saw his home on the point and sat on a park bench listening to waves crash over black rocks—simple and perfect.
Rainy Kennebunkport was saved by Brewed Awakening, a coffee shop-slash-animal farm (yes, goats and chickens!) where bagel sandwiches ruled the day.
We also stopped at The Holy Donut for their famous potato donuts. Rain or shine, they’re worth the hype.
Bar Harbor: A Grand Finale
Bar Harbor was the crown jewel of our trip. The Claremont Hotel transported us straight into a rom-com, complete with an old station wagon out front and dreamy porches overlooking the ocean.
The on-site restaurant, Little Fern? Five stars. The Botanika spa? Tranquility defined. The Fish Camp? Cozy perfection and great snacks. The salt glass I found on the shore? My new favorite souvenir.
We hiked Acadia National Park, rain and all, with Joshua Pond Trail being a clear winner. Three miles of rugged beauty and wooden bridges made every step worth it. We hiked to one of Maine’s lighthouses called Bass Harbor Head Lighthouse in Acadia. A little slippery rock climb in the rain but worth it!
Leaving The Claremont was hard. We debated extending our stay and skipping Portland altogether, but alas, responsibilities called.
Maine, You’ve Got My Heart
From driving Duck Boats to discovering the flavors of maple syrup, this trip had it all: food, foliage, and a fair share of laughs. Maine, Boston, Vermont—consider us smitten. We’ll be back, and next time, I’m buying that flannel.
Until then, cheers to the memories, the lobster gnocchi, and surviving my stint as a Duck Boat captain!
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