Eat, Shop & Sightsee
Food scene
Restaurants, delis and sandwich shops.
Serves pub fare, an endless choice of craft beers, and generous cocktails. Indoor and outdoor seating right on the picturesque Connecticut River.
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Whetstone Station Restaurant and Brewery
36 Bridge StServes pub fare, an endless choice of craft beers, and generous cocktails. Indoor and outdoor seating right on the picturesque Connecticut River.
Light, airy and spacious seating. Indoor and outdoor dining on the beautiful West River. Very family friendly and can accommodate large groups.
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Marina
28 Spring Tree RdLight, airy and spacious seating. Indoor and outdoor dining on the beautiful West River. Very family friendly and can accommodate large groups.
Located in downtown Brattleboro, this little gem offers intimate dining and amazing dishes. Patio seating in warm weather.
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Peter Havens Restaurant
32 Elliot StLocated in downtown Brattleboro, this little gem offers intimate dining and amazing dishes. Patio seating in warm weather.
This is our favorite restaurant! Make a reservation because you can be waiting up to an hour for a table, but it’s worth it. The food is amazingly delicious (ever-changing menu that utilizes local ingredients) and the service is the best.
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Hope & Olive
44 Hope StThis is our favorite restaurant! Make a reservation because you can be waiting up to an hour for a table, but it’s worth it. The food is amazingly delicious (ever-changing menu that utilizes local ingredients) and the service is the best.
Delicious deli food, sandwiches, and desserts. Offers a variety of local and New England made products. A favorite with locals and visitors.
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The Vermont Country Deli
436 Western AveDelicious deli food, sandwiches, and desserts. Offers a variety of local and New England made products. A favorite with locals and visitors.
Natural foods co-op with many local and Vermont/New England made products. Deli counter with endless choices, seafood counter, health and beauty aids, whatever you want, they have it. Large area for eating in, and an outside patio area, right in downtown Brattleboro.
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Brattleboro Food Co-Op
2 Main StNatural foods co-op with many local and Vermont/New England made products. Deli counter with endless choices, seafood counter, health and beauty aids, whatever you want, they have it. Large area for eating in, and an outside patio area, right in downtown Brattleboro.
Delicious sandwiches, soups, and desserts in downtown Brattleboro.
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Amy's Bakery Arts Cafe
113 Main StDelicious sandwiches, soups, and desserts in downtown Brattleboro.
Echo Restaurant & Lounge
69 Main StPopular downtown Brattleboro restaurant.
A Vermont Table
A high end, farm to table dining experience.
Delicious homemade sandwiches, soups, and prepared foods ideal for grabbing a tasty dinner when you don’t want to cook.
Guilford Country Store
Delicious homemade sandwiches, soups, and prepared foods ideal for grabbing a tasty dinner when you don’t want to cook.
Sightseeing
Hiking trails, canoe & kayak rentals, and places to take the kids.
This place has a great history and numerous trails that offer spectacular views. If feeling really ambitious, you can hike over to Hinsdale and find yourself on top of Mount Wantastiquet. It’s a totally doable hike-I did it with a bunch of 6th graders. **The second photo is not even of the area. Not sure why or where they got that photo!**
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Madame Sherri Forest
This place has a great history and numerous trails that offer spectacular views. If feeling really ambitious, you can hike over to Hinsdale and find yourself on top of Mount Wantastiquet. It’s a totally doable hike-I did it with a bunch of 6th graders. **The second photo is not even of the area. Not sure why or where they got that photo!**
Enjoy a scenic, flat, 1.3 mile walk (from our house) to the covered bridge and dam. Our area is popular with bikers, joggers, and walkers for its miles of flat, quiet, dirt roads. Swimming at the dam in the summer.
Green River Covered Bridge ,
Stage RoadEnjoy a scenic, flat, 1.3 mile walk (from our house) to the covered bridge and dam. Our area is popular with bikers, joggers, and walkers for its miles of flat, quiet, dirt roads. Swimming at the dam in the summer.
Black Mountain Trailhead
1933 Black Mountain RdLovely, kid-friendly hike with awesome views.
Rent canoes and kayaks and paddle on the West and Connecticut Rivers.
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Vermont Canoe Touring Center
451 Putney RdRent canoes and kayaks and paddle on the West and Connecticut Rivers.
Bring the kids to the petting farm, then skip over to the Grafton Cheese Company for shopping and local items. The farm hosts a summer goat yoga series, which is always fun, a food truck roundup and numerous other events. Access 9 miles of the Retreat Trail system.
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Retreat Farm
45 Farmhouse SqBring the kids to the petting farm, then skip over to the Grafton Cheese Company for shopping and local items. The farm hosts a summer goat yoga series, which is always fun, a food truck roundup and numerous other events. Access 9 miles of the Retreat Trail system.
Visit the historic Retreat Tower, unfortunately the structure is closed, and walk for miles on the Retreat Trail system. The famous Harris Hill ski jump is situated on one of the many trails. Every February it hosts ski jumpers from around the world.
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Retreat Tower
Reservoir LoopVisit the historic Retreat Tower, unfortunately the structure is closed, and walk for miles on the Retreat Trail system. The famous Harris Hill ski jump is situated on one of the many trails. Every February it hosts ski jumpers from around the world.
Every February Harris Hill hosts ski jumping competitors from around the world. It’s also located on 9 miles of the Retreat Trail system.
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Harris Hill Ski Jump
Cedar StreetEvery February Harris Hill hosts ski jumping competitors from around the world. It’s also located on 9 miles of the Retreat Trail system.
Spend a couple hours hiking the mountain and enjoy the amazing view of Brattleboro. You can continue your hike into New Hampshire and wind up at Madame Sheri’s Forest in West Chesterfield.
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Wantastiquet Mountain
Spend a couple hours hiking the mountain and enjoy the amazing view of Brattleboro. You can continue your hike into New Hampshire and wind up at Madame Sheri’s Forest in West Chesterfield.
Molly Stark State Park
705 VT-9Lovely hike to fire tower for spectacular views.
Sweet Pond
Nice and easy family friendly hike around Sweet Pond, right here in Guilford.
Shopping
Enormous amount of quality second hand items for sale. I could spend hours here.
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Twice Upon A Time Antiques
63 Main StEnormous amount of quality second hand items for sale. I could spend hours here.
Amazing art, beautiful, handcrafted jewelry, and items for the home.
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Gallery In the Woods
145 Main StAmazing art, beautiful, handcrafted jewelry, and items for the home.
Funky, quirky shop. I always buy something when I stop in here, and the prices are amazingly low.
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Experienced Goods Thrift Store
80 Flat StFunky, quirky shop. I always buy something when I stop in here, and the prices are amazingly low.
Grafton Village Cheese Company
400 Linden StLocal cheeses, wines, and gifts.
Altiplano
42 Elliot StBeautiful clothing, jewelry, and gifts.
Yankee Candle
25 Greenfield RdEnormous flagship store in Deerfield, MA..
Museum/ Cultural
Ever-changing art exhibits and events in beautiful, historic train station, right in downtown Brattleboro.
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Brattleboro Museum & Art Center
10 Vernon StEver-changing art exhibits and events in beautiful, historic train station, right in downtown Brattleboro.
Four screen movie theater in a GORGEOUS, historic Art Deco building, right in downtown Brattleboro.
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Latchis Theatre
50 Main StFour screen movie theater in a GORGEOUS, historic Art Deco building, right in downtown Brattleboro.
Amazing, one of a kind art installations located in a series of old brick factory buildings in North Adams, MA.. Highly recommend.
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MASS MoCA
1040 Mass MoCA WayAmazing, one of a kind art installations located in a series of old brick factory buildings in North Adams, MA.. Highly recommend.
The Clark Art Institute
225 South StFarmers’ Market
Beautiful congregation of farmers, food vendors and artisans in a gorgeous spot along the Whetstone River. Must check out if in the area. In the spring they have a lovely May Day celebration with song and dance around the May pole.
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Brattleboro Farmers Market
570 Western AveBeautiful congregation of farmers, food vendors and artisans in a gorgeous spot along the Whetstone River. Must check out if in the area. In the spring they have a lovely May Day celebration with song and dance around the May pole.
Unique Places
Unique places in the area to feast your eyes.
Old railroad bridge turned into magical garden in Shelburne Falls, MA.
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Bridge of Flowers
Bridge of FlowersOld railroad bridge turned into magical garden in Shelburne Falls, MA.
A must see. Gardens entwined with one of kind sculptures and stonework in Goshen, MA..
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Three Sisters Sanctuary
188 Cape StA must see. Gardens entwined with one of kind sculptures and stonework in Goshen, MA..
Kids and adults love the butterfly museum in South Deerfield, MA..
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Čarobna krila leptira konzervatorij
281 Greenfield RdKids and adults love the butterfly museum in South Deerfield, MA..
Amazing plants from around the world in gorgeous metal framed glass greenhouses. In early March the spring bulb show is a must see! Located on Smith College campus in Northampton, MA..
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Smith College Botanic Garden
16 College LnAmazing plants from around the world in gorgeous metal framed glass greenhouses. In early March the spring bulb show is a must see! Located on Smith College campus in Northampton, MA..