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Brattleboro

Brattleboro, VT is a charming town nestled in the Green Mountains. Known for its vibrant arts scene, quirky shops, and delicious farm-to-table eateries. Explore the colorful downtown area, take a stroll along the Connecticut River, or hike up Mount Wantastiquet for breathtaking views. Don't forget to check out the famous farmers' market!

Recommendations

Outdoor4.6/5

Fort Dummer State Park

Welcome to Fort Dummer State Park, where history meets nature in Guilford, Vermont! Explore the remains of a colonial fort, hike scenic trails, and enjoy a picnic by the peaceful river. Don't forget your camera for Instagram-worthy shots! Located at 517 Old Guilford Rd, Guilford, VT 05301, it's the perfect spot for a day trip.

Culture4.6/5

Brattleboro Museum & Art Center

Step into a world of creativity at Brattleboro Museum & Art Center! Located in the charming town of Brattleboro, Vermont, this museum showcases contemporary art from local and international artists. From thought-provoking exhibits to interactive installations, there's something for everyone to enjoy. Don't miss out on this cultural gem during your travels!

Landmark4.6/5

Historic Creamery Covered Bridge

Step into a charming slice of history at Creamery Covered Bridge in Brattleboro, Vermont. Built in 1879, this iconic red bridge spans the Whetstone Brook, offering a picturesque backdrop for photos. Take a leisurely stroll through this quintessential New England landmark and feel like you've traveled back in time.

Landmark4.6/5

Brattleboro Outdoor/Summer Farmer's Market

Step into a vibrant world of fresh produce, local crafts, and friendly faces at Brattleboro Outdoor Farmer's Market. Located in West Brattleboro, VT, this market is a must-visit for any traveler looking to experience the best of Vermont's farm-to-table culture. Don't forget your reusable tote bag and appetite for delicious treats!

Eat$$$$4.8/5

Peter Havens Restaurant

Peter Havens Restaurant in Brattleboro, VT is a charming spot serving up delicious New American cuisine with a French twist. From the cozy atmosphere to the mouthwatering dishes, every detail is thoughtfully curated to create a memorable dining experience. Don't miss out on their extensive wine list and creative cocktails!

Eat$$$4/5

Whetstone Station

Looking for a cozy spot to grab a bite in Brattleboro, VT? Look no further than Whetstone Station! Located right by the river, this restaurant offers delicious comfort food, craft beers, and a chill atmosphere. Don't miss out on their outdoor seating with stunning views. Perfect pit stop for any hungry traveler!

Outdoor$$$4.2/5

The Marina

Experience riverside charm at The Marina on 28 Spring Tree Rd in Brattleboro, VT. Dock your boat and explore the quaint town filled with local shops and delicious eateries. Don't forget to catch a stunning sunset over the water before heading back to your cozy accommodations. This is the perfect spot for a relaxing getaway by the water.

Eat$$$$4.8/5

T. J. Buckley's

T.J. Buckley's in Brattleboro, VT is a cozy spot serving up delicious Irish-inspired fare. The atmosphere is welcoming, with friendly staff and a lively crowd. Indulge in their hearty shepherd's pie or tasty fish and chips. Don't forget to pair your meal with a refreshing pint of Guinness. Sláinte!

Eat$$$4.7/5

The Vermont Country Deli

Looking for a taste of Vermont? Head to The Vermont Country Deli in Brattleboro for a delicious selection of local cheeses, baked goods, and sandwiches. Don't miss their famous maple syrup treats! Located at 436 Western Ave, it's a must-stop for any foodie on the go.

Eat$$$4.6/5

Amy's Bakery Arts Cafe

Located on Main Street in Brattleboro, Amy's Bakery Arts Cafe is a charming spot to grab a delicious pastry and coffee. The cozy atmosphere and friendly staff make it a perfect stop for weary travelers looking for a tasty snack. Don't miss the opportunity to try their famous homemade breads and pastries!

Cafe$$4.6/5

Mocha Joe's Cafe

Calling all coffee lovers! Mocha Joe's Cafe on Main Street in Brattleboro is a must-visit for some seriously good brews. With cozy vibes and friendly baristas, this spot is perfect for fueling up before exploring the charming town. Don't miss out on their delicious pastries too!

Stays

Stay4.9/5

Chesterfield Inn

Nestled in the quaint town of West Chesterfield, NH, Chesterfield Inn is the ultimate cozy retreat. With luxurious accommodations, delicious farm-to-table dining, and picturesque views of the surrounding countryside, this charming inn is the perfect escape for travelers seeking relaxation and comfort. Don't miss out on this hidden gem!

Stay4.65/5

Inn on Putney Road Bed and Breakfast

Welcome to Inn on Putney Road Bed and Breakfast in Brattleboro, VT! This charming B&B boasts cozy rooms, delicious breakfast, and a prime location near hiking trails and local attractions. With friendly hosts and delightful amenities, you'll feel right at home during your stay. Don't miss the chance to relax and unwind in this lovely Vermont getaway!

Stay4.05/5

Hampton Inn Brattleboro

Welcome to Hampton Inn Brattleboro, where cozy comfort meets Vermont charm. Located on Putney Road, this hotel offers easy access to nearby attractions like Brattleboro Museum & Art Center and Mount Snow. Relax in spacious rooms, fuel up with our complimentary breakfast, and unwind in the indoor pool. Perfect for a memorable getaway in beautiful Brattleboro!

Stay3.15/5

The Covered Bridge Inn

Step back in time at The Covered Bridge Inn, a quaint and charming getaway nestled in Brattleboro, VT. This cozy spot on Putney Rd offers a unique experience with its historic covered bridge on site. A perfect blend of old-world charm and modern comfort awaits you at this hidden gem in New England.

Stay4.3/5

Latchis Hotel

Step inside Latchis Hotel and enter a world where vintage charm meets modern comfort. Located in the heart of Brattleboro, VT, this historic hotel offers cozy rooms, a convenient location on Main Street, and a quirky Art Deco vibe. Enjoy a unique stay in this boutique hotel that's perfect for exploring the town's artsy and eclectic atmosphere.

Things To Do
Provided by

5/5

2 h

Mindful Forest Escape: Rebalance, reflect and connect

Step away from the noise of everyday life and reconnect with the soothing rhythms of nature on a deeply transformative forest immersion experience. Under expert guidance, you’ll embark on a mindful journey through Vermont’s stunning landscapes, where the forest becomes your sanctuary, and every moment invites you to pause, reflect, and breathe. Whether you’re new to meditation or a seasoned practitioner, this experience caters to all. Through gentle mindfulness practices, sensory explorations, and playful invitations, you’ll learn how to connect with nature in a more intentional, grounding way. This experience isn’t a hike—it’s an opportunity for personal reflection, a chance to leave the stresses of the world behind and step into the quietude of the present. Guests often leave feeling calmer, more centered, and with a renewed appreciation for the world around them, ready to integrate this peaceful presence into their daily lives.

$55.00

5/5

Vermont Wayfinders Fall Foliage Private Tour

There’s nothing like fall in Vermont! The crisp air, the burst of color from maple leaves, and sunlight filtering through the trees make every back road feel like an adventure. Be sure to check out the Vermont Wayfinders website for more information on tours and availability, including add-on options like heading to the top of Killington or going for a horse-drawn carriage ride. Your curated tour takes you through the most scenic routes during foliage season. Whether you’re looking for panoramic views, covered bridges framed by colorful leaves, or charming villages bursting with fall vibes, we put together each itinerary to give you the ultimate Vermont fall experience. Tour Highlights: - Breathtaking foliage views from iconic overlooks and winding back roads - Visits to cozy Vermont towns - Stops at local farms, breweries and hidden vistas - Chances to wander near fields and forests and capture postcard-worthy photos

$1,008.00

4.7/5

12 h

Fall Foliage Scenic Day Trip to Vermont and Western MA with Stops

Discover the vibrant colors of autumn on a Fall Foliage Day Trip from Boston through Southern Vermont and Western Massachusetts. Your journey begins in Western Massachusetts with scenic stops at the French King Bridge, Mineral Road Bridge, and historic Cabot Camp—each offering sweeping views of brilliant foliage along the Connecticut River. From there, we’ll head north into Southern Vermont, where the season’s beauty unfolds at the charming Creamery Covered Bridge and the Hogback Mountain General Store and Scenic Overlook. Along the way, enjoy a relaxing lunch and time to take in the crisp mountain air. On the return trip to Boston, we’ll visit the Yankee Candle Flagship Store, where you can explore its signature scents and seasonal displays—an aromatic highlight to end the day. Don’t miss this unforgettable autumn escape from Boston, filled with breathtaking views, charming stops, and the very best of New England’s fall foliage.

$149.00

48 h

Cycling New Hampshire's Covered Bridges

This incredible 2-day bike tour takes you to twelve of New Hampshire’s beautiful, historic covered bridges as you cycle through gorgeous mountain vistas, passing sparking lakes, rivers and streams. Everything is included, overnight lodging, 2 lunches, 1 breakfast, bike rental and helmet, Van support, tour guides and more!