With its classic Main Street retail district and scenic location at the convergence of the West and Connecticut Rivers, the southern Vermont city of Brattleboro attracts visitors looking for a lively and culturally rich destination with all the charm of a New England small town. It's a hub for hikers, cyclists, and kayakers, too, with recreational opportunities on the city's fringes and even right downtown. And that means there are plentiful opportunities to work up an appetite—fuel your adventures at one of Brattleboro's seven top dining spots.
True to its name, The Marina is more than a restaurant. You can rent kayaks right here, where the West River empties into the Connecticut, and go for a paddle before returning to reward your exertion with popular selections from the waterside restaurant's extensive menu. Expect a wait if you want a seat on the canopy-shaded outdoor deck on a perfect summer day. Never fear, though. There are water views from practically every inside seat, too. When a sign on the table has to implore you not to steal the vibrant cloth napkins, you know they're a special touch… and they're necessary for tidying up after you devour a juicy burger or fried seafood feast. We like the grilled, lime-marinated shrimp, and so does Food Network star, Rachael Ray.
You'll need reservations at Brattleboro's enduring date night spot, where chef-owner Zach Corbin stays true to his Vermont roots, utilizing the state's bounty to create dishes that are as eye-pleasing as they are delicious. The softly lit, windowed dining room has just 10 tables, which ensures an intimate experience. A few seats at the bar allow the restaurant to accommodate extra diners, and the patio, with its own menu, specials, and outdoor bar, is the place to be on warm summer eves. A beautifully composed wine list and cocktail line-up give you plenty of sipping options while you're perusing the menu, which shifts with the seasons to showcase the best of what's fresh-made, harvested, and caught.
If you're a beer fan in Brattleboro, this restaurant is known for its always-innovating, on-site brewery, and rooftop beer garden is a must stop. And even if you'd instead sip wine, Vermont-made alcoholic cider, or froufrou cocktails, you'll be a happy camper here, especially once you witness the view. Whetstone Station Restaurant and Brewery overlooks the Connecticut River, and sunsets in all seasons are magnificent. Firelight, both outdoors on the rooftop and inside, adds a touch of magic and warmth. The menu? Not your average brewpub fare. Try dishes featuring seasonal ingredients like locally made bratwurst with beer-braised cabbage or strip steak rubbed with spices and local coffee and drizzled with maple bourbon gravy.
Authenticity reigns at this little cocina, where Mucuy Bolles and Christian Makay carry on the ancient cooking traditions learned from her mother, Alejandra Bolles, who was born in Mexico's land of the Maya. The pair even earned a coveted "Best Chef: Northeast" nomination from the James Beard Foundation in 2017. Don't agonize over empanadas vs. tamales. Try both. But save room for the Dulce de Leche dessert. Everything is made fresh, the flavors are enticing, and you're in for a unique time travel tasting experience.
When you crave a truly immersive and unique dining experience, reserve one of the eight tables inside this 1925 Worcester Dining Car turned fine dining restaurant. An open kitchen allows you to spy on the magic, as chef-owner Michael Fuller crafts meals to remember. He's been cooking with unusual ingredients farmed and foraged locally for three decades, paving the way for the now omnipresent farm-to-table movement in Vermont. Expect a small menu of exquisitely prepared dishes.
Want to pick up yummy sandwiches and sweet treats to pack along on your hike, bike ride, or paddling trip? Everything you need for a gourmet picnic awaits at Vermont Country Deli (and its market across the street) in Brattleboro. They're open late during ski season, too, when you've worked up an appetite on the slopes. Sandwiches here are super-hearty, and they're made, of course, with an ingredient Vermont is famous for: cheese. And if you can resist the pastries and cookies, you are a rare person, indeed.
This roadside BBQ stand may not look like much as you're motoring past, but there's a reason Top of the Hill Grill has become a Brattleboro landmark. All of the meat—tender pulled pork, glide-off-the-bone ribs—are hickory-smoked right on-site. Sausages are made here, too, as are all of the salads, sides, and desserts (chipotle brownies are a kick!). The menu's more diversified than you'd imagine, with Cajun, Mexican, and even many vegetarian options. Order at the window, then claim a table in the screened, stove-warmed deckhouse or on the outdoor patio, and savor the smoky goodness and the river and hillside views.