There’s just something magical about fall in New England. The air turns crisp, the trees glow with shades of red and gold, and every small town smells like apples, cinnamon, and something delicious baking in the oven. Whether you’re cruising the coast or exploring winding mountain roads, one thing’s for sure—New England is as much a food destination as it is a scenic one.
On our recent trip, we set out to discover the absolute best bites the region has to offer—from buttery lobster rolls in Maine to creamy chowder in Boston and sweet maple creemees in Vermont. This itinerary is for anyone who believes that the best way to experience a place is through its food.
So grab your appetite (and maybe a pair of stretchy pants) and join us on our “Best Fall New England Eatinerary”—five unforgettable food stops that deserve a spot on your bucket list.
The Best Clam Chowder – Boston Sail Loft – Boston,MA
On our trip to Boston last fall, we set out on a mission: to find the best clam chowder in the city. Our search led us to a small, unassuming building with an oval-shaped sign that read Boston Sail Loft. It seemed like the perfect place to kick off our chowder adventure. Little did we know, it would also be the first stop, the last stop, and every craving in between.
The chowder here was everything we hoped for and more. Creamy with just the right thickness, packed with tender clams, and finished with perfectly cooked potatoes that brought the whole bowl together. Honestly, it felt like we had stepped straight into clam chowder heaven.
At first, we thought we had uncovered another hidden gem. But as it turns out, the Boston Sail Loft is already a legend. Their chowder has been featured on The Drew Barrymore Show and The Today Show, and it even won “Best of Boston” in 2018 & 2019. So yes—we may have been late to the party, but this classic is still going strong.
If Boston (or anywhere in New England) is on your itinerary, make sure this spot is at the top of your list. Trust us, one spoonful and you’ll understand why.
📍80 Atlantic Ave, Boston, MA
https://www.thebostonsailloft.com
The Best Pizza – Joanies Pizza – Chelmsford, MA
Whenever we visit a new area, one of our favorite traditions is tracking down the best slice of pizza we can find. A little research led us to one spot that kept popping up again and again. Even though it was about 35 minutes outside of Boston, curiosity got the best of us and we decided to see what all the fuss was about.
When we pulled up, we found ourselves in front of a small strip mall that looked just like countless others. For a moment we hesitated, was this really going to be worth the drive? But since we’d already made the trip, we figured we might as well give it a shot. And wow, are we glad we did.
The pizza was outstanding. We ordered the 16” Joanie Pepperoni. A New York–style pie with a tangy, savory red sauce, loaded with pepperoni, sprinkled with fresh garlic, and finished with the perfect crispy crust. Every bite was spot on. Honestly? 10/10, no notes. We’d make the drive again in a heartbeat.
Fun fact: Dave Portnoy gave this pizza an 8.4—so you know it’s the real deal.
📍83 Parkhurst Rd #5, Chelmsford, MA
The Best Lobster Roll – The High Roller – Portland Maine
If you’ve ever thought, “I’d love a lobster roll… but actually, I’d love three,” then we’ve found the spot for you. The High Roller in Portland, Maine, takes lobster rolls to a whole new level with their lobster roll flights. That’s right—flights of perfectly crafted lobster rolls, each served in different styles and flavors. Hot or cold, creamy or buttery, they have every version you could dream of, and each one is just as delicious as the next.
Now, here’s where we give you the inside scoop: you cannot leave without ordering the lobster grilled cheese. This masterpiece combines rich cheddar and melty Swiss between buttery toasted bread, with sweet, tender lobster tucked inside. It’s indulgent, it’s unforgettable, and honestly, it might be one of the greatest creations known to mankind.
📍104 Exchange St, Portland ME
The Best Sandwich – Vermont Country Deli – Brattleboro, VT
Have you ever thought back to the kind of sandwich your mom used to make when you were a kid? You’d come inside after running around with friends, gulp down a glass of Hi-C between heavy breaths, and then sit down to that simple but perfect sandwich. Just meat and cheese on bread, maybe a little mustard or mayo—but that first bite was magic. Fresh, balanced, and unforgettable.
Now, imagine that same nostalgic feeling, only elevated and made to order. That’s exactly what you’ll find at the Vermont Country Deli. Tucked a bit off the beaten path, this spot is absolutely worth the detour. Their sandwiches capture that perfect comfort-food balance, while still delivering on freshness and flavor that feel gourmet.
And while the sandwiches are the star of the show, the menu goes well beyond that. Think bubbling baked mac and cheese that could win anyone over, a full deli case with countless options, and a bakery packed with indulgent treats. From cookies in every flavor to giant éclairs filled with house-made French custard, plus a wide variety of artisanal breads—this place truly has it all.
https://www.vermontcountrydeli.com
📍436 Western Ave, Brattleboro, VT
The Best Maple Creemee – Mad Hatter’s Scoops – Killington VT
We didn’t realize it at the time, but Vermont’s famous maple creemee has quite a history. Back in 1981, the Rutland County Maple Producers asked a local dairy to swap the sugar in their soft-serve ice cream with maple syrup. Just like that, the maple creemee was born. A sweet, creamy classic that’s been a Vermont staple ever since.
Now that you know the backstory, let’s talk about the real star: Mad Hatter’s Scoops. For our money, they serve up the best maple creemee around. Made in-house with First Chair Syrup, their version is rich, velvety, and the perfect balance of maple sweetness. It’s a treat that hits the spot no matter your age.
If you find yourself anywhere near Killington, make sure Mad Hatter’s is on your itinerary. It’s an absolute must!
📍40 Summit Rd, Killington, VT
https://www.madhatterskillington.com
From chowder by the harbor to maple creemees in the mountains, New England in the fall is a food lover’s dream. Each stop on this list serves up more than just a great meal—it’s a taste of the region’s charm, tradition, and creativity.
Whether you’re planning a full road trip through all six states or just sneaking away for a weekend, these destinations are proof that every bite tells a story—and in New England, that story is delicious.
So the next time you’re chasing fall colors, make sure to chase a few of these flavors too. Trust us—you’ll leave full, happy, and already planning your next trip back.