New England in the fall is nothing short of magical. Between the crisp autumn air, the vibrant foliage, and the mix of historic charm and modern flavors, it’s the perfect destination for travelers who love pairing scenic drives with unforgettable food experiences. On our recent trip, we set out to explore three of New England’s gems- Boston, Vermont, and Portland. Each one offering its own unique blend of culture, cuisine, and character. (Click link below for our instagram video)
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In Boston, we uncovered chowder worth writing home about and dove into the world of craft beer at one of the country’s most iconic breweries.
Vermont welcomed us with cozy cabins, scenic drives along Route 100, and comfort food elevated to new heights.
In Portland, Maine, we indulged in lobster rolls, set sail for a wine-tasting adventure, and explored one of the most walkable and food-friendly small cities in America.
Whether you’re planning a long weekend or a full road trip, this guide highlights some of the best eats, experiences, and stays we discovered along the way.
BOSTON
Best Place To Eat:
Boston Sail Loft – Boston, MA
On our trip to Boston, we set out to find the city’s best clam chowder and we didn’t have to look far. The Boston Sail Loft, a small unassuming spot by the water, ended up being the first and only stop we needed.
Their chowder was perfection: creamy, loaded with tender clams, and balanced with just the right amount of potatoes. It truly felt like clam chowder heaven.
Far from a hidden gem, this place is a Boston icon, featured on The Drew Barrymore Show and The Today Show, and winner of “Best of Boston” in 2018 & 2019.
If you’re visiting Boston or anywhere in New England, make sure this spot is on your list. One spoonful and you’ll see why.
Best Experience:
The Sam Adams Brewery Tour, Boston,MA
If you’re planning a trip to Boston and love craft beer, the Sam Adams Beyond the Brewhouse Tour at their Jamaica Plain brewery is an absolute must. For just $25, this experience goes far beyond your typical brewery tour and offers a fascinating, behind-the-scenes look at how one of America’s most iconic breweries continues to innovate.
The tour begins with an insider’s look at the brewing process, giving visitors a chance to see how Sam Adams blends tradition with experimentation. Along the way, you’ll discover exciting new beer styles in development and get a close-up view of their unique cask-aging program.
One of the highlights is the Bier Keller, where research and development beers rest in casks sourced from around the globe. Walking through this space feels like stepping into the heart of their creativity—where innovation, patience, and craftsmanship come together. And of course, there are plenty of samples to enjoy throughout the experience, making it as delicious as it is educational.
Whether you’re a long-time Sam Adams fan or just beginning your craft beer journey, the Beyond the Brewhouse Tour offers a fun, flavorful, and immersive way to deepen your appreciation for brewing. It’s a perfect mix of history, innovation, and most importantly, great beer.
Where To Stay:
When planning a trip to Boston, we highly recommend staying in the North End, Downtown, or West End neighborhoods. These areas offer the best of the city right at your doorstep, with walkable streets that lead you to iconic landmarks like Quincy Market, TD Garden, and the historic Paul Revere House. Staying in these neighborhoods not only keeps you close to major attractions but also allows you to truly soak in the charm and energy of the city.
One important tip to keep in mind: always check for resort and parking fees when booking your hotel. While Boston has plenty of fantastic accommodations, these extra charges can add up quickly and may significantly impact your budget if overlooked. Doing a little research ahead of time can help you find the perfect spot without any surprises.
Pro-tips:
Check out Emmets Pub & Restaurant for the best Irish Coffee we’ve ever had!
VERMONT
Best Place To Eat:
Vermont Country Deli – Brattleboro, VT
If you’ve ever longed for that simple, perfect sandwich from childhood—fresh bread, the right balance of meat and cheese, and just enough mayo or mustard—the Vermont Country Deli brings that nostalgia to life, only better.
While the sandwiches are the star, this deli is so much more. From bubbling baked mac and cheese to a bakery stocked with cookies, éclairs filled with French custard, and artisanal breads, it’s worth the detour. Comfort food meets gourmet, all in one stop.
Best Experience:
For a classic New England autumn drive, Vermont’s Route 100 is hard to beat. This scenic two-lane highway winds through charming towns, rolling farmland, and forested mountain slopes that explode in red, orange, and gold each fall.
After our stop at the Vermont Country Deli, we continued our journey by picking up Route 100 in Ludlow and driving all the way north to Chittenden. The drive was wonderfully easy, allowing us to fully take in the spectacular, breathtaking views along the way.
Peak season for viewing is between late September and Mid October. We chose to go the first week of October and were not disappointed.
Whether you’re a leaf-peeping enthusiast or just looking for a peaceful fall escape, Route 100 delivers a quintessential Vermont experience that captures the beauty and charm of autumn in New England.
Where To Stay:
On our recent trip to Killington, we stayed in an Airbnb about 15 minutes north, tucked away in the quiet town of Chittenden. To say this place was amazing would be an understatement—it truly felt like a home away from home.
Hosted by Ann, the cabin is a remote little hideaway surrounded by woods, complete with a beautiful fireplace that sets the perfect cozy atmosphere. Whether you’re returning from a day on the slopes or simply looking for a peaceful escape, this cabin delivers the ultimate Vermont retreat.
If you’re planning a visit, you’ll want to book early—reservations for peak season go quickly. You can check availability here. Trust us, this is the kind of place you’ll want to return to again and again.
Pro-tip:
For an amazing treat check out Mad Hatter Scoops in Killington for the best maple creemee in Vermont
PORTLAND
Best Place To Eat:
The High Roller – Portland, ME
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.
Best Experience:
Wine Wise Events – Portland, ME
There are food and wine experiences you remember, and then there are the ones that stay with you forever. Last fall, we joined a Wine Wise Events sail in Portland, Maine, and it quickly became one of those unforgettable afternoons.
Picture this: the sun high in the sky over the water, a gorgeous sailboat cutting through the harbor, glasses of French wine in hand, and the salty breeze mixing with aromas from the galley. Add in the guidance of our sommelier Erica Archer and exquisite bites from Chef Sansonetti of Chaval (a James Beard finalist), and you’ve got the makings of pure magic.
The afternoon was as educational as it was indulgent. Erica walked us through each pour, teaching us how to taste wine properly and appreciate the layers of aroma and flavor. Each of the five wines was paired with a dish so thoughtfully prepared that every bite felt like an extension of the glass.
By the end of the sail, it was clear this wasn’t just a wine tasting. It was a journey across regions, flavors, and traditions, all while surrounded by the beauty of the Maine coast.
Where To Stay:
When planning a trip to Portland, location makes all the difference. We recommend booking your stay in Downtown, the East End, or East Bayside. These neighborhoods put you right in the heart of the action, with easy access to the waterfront, a huge variety of breweries, and plenty of restaurants and shops to explore on foot.
One of the things we loved most about Portland is how walkable and safe the city felt. Whether you’re strolling along the cobblestone streets of the Old Port or heading out for a brewery crawl in East Bayside, you’ll find it easy (and fun!) to get around without needing your car.
Pro-tip:
Make sure you hit up Gilberts Chowder House for their seafood chowder. It is a deliciously warm meal on a rainy day!
In Conclusion
From the bustling streets of Boston to the winding roads of Vermont and the coastal charm of Portland, our New England adventure was the perfect mix of food, adventure, and breathtaking scenery. Each stop offered something unforgettable! Whether it was chowder by the harbor, a drive framed by golden foliage, or a wine cruise with ocean views. If you’re planning a trip to New England, consider weaving all three destinations into your itinerary. Trust us: the combination of flavors, experiences, and landscapes will leave you planning your return before you’ve even left.