what to do in the area

You’ll find our suggestions for adventures, fun activities, restaurants, and important information such as local health services listed below.

Adventures

Brattleboro.com – Experience everything that Brattleboro has to offer. This website has an excellent calendar of area events.

Art:

  • Brattleboro Museum & Art Center (Brattleboro, VT)

  • Gallery Walk (Brattleboro, VT) – Stroll from art exhibit to exhibit every first Friday night in downtown Brattleboro. Often there’s music in the streets and delicious pop-up food vendors.

Cheese:

  • Grafton Village Cheese Company (Brattleboro, VT) – Best cheese! Located next to the Retreat Farm where you can visit animals and walk trails.

  • Brattleboro Food Co-Op Cheese Counter (Brattleboro, VT) – try Lazy Lady Farm’s “The Thin Red Line” and the Vermont Farmstead Cheese Company’s LILLÉ (COULOMMIERS). Pick up a seeded baguette by Red Hen Baking in the next aisle and you will be in for a wonderful afternoon.

Day Trips:

  • Manchester, VT (1 hour North) – great outlet shopping and incredible restaurants

  • Northampton, MA (40 minutes South) – fun college town that has it all

  • Keene, NH (25 minutes East) – hikes, shopping, restaurants

  • Woodstock, VT (1hr 15 minutes North) – quintessential upscale Vermont with delicious restaurants and activities like Falconry.

Farms:

  • Scott Farm Orchard (Dummerston, VT) – Historic apple farm with over 70 varieties of heirloom apples. The movie The Cider House Rules was filmed here. They also host stone wall building classes. It's a cool and beautiful place to visit.

  • Retreat Farm (Brattleboro, VT) – Visit cute animals, ice skate on the pond, hike or snowshoe their 10 mile trails. They also have a popular food truck event with outdoor music.

  • Green Mountain Orchards (Putney, VT) – The most beautiful apple orchard for in-season fruit picking, Vermont products, and fresh-pressed cider.

Fitness:

  • Inner Heat Yoga (Brattleboro, VT) – Offers a variety of yoga and pilates classes just a 15 minute drive into town.

  • New England Center for Circus Arts (Brattleboro, VT) – NECCA offers private lessons if booked in advance for everything your heart desires including aerial silks/rope, trapeze, trampoline wall, and so much more. Visit their website and look under private lessons to book. They also have drop-in classes for aerial yoga and short day to week intensives.

  • Shiva Shakti Power Yoga (Northampton, MA) – While this is a 40 minute drive South from the farmstead, it is located in a college town that has fantastic restaurants. This is by far the best hot vinyasa yoga class we’ve ever attended. It's similar to Modo Studio Yoga if you're familiar. The studio is heated to the mid 90's and you'll follow a rigorous vinyasa yoga flow – if you require mats, yogitoes towel, etc they have all that available to rent. When you go for the first time, just note that the entrance is not on the street – it's around back through the parking lot area behind a lattice fence. Do not forget to drink water before and after!

Flea Markets:

  • The Original Newfane Flea Market (Newfane, VT) – The Newfane Flea Market, originally established in 1967 is Vermont’s first and longest running Flea Market. In its height, the Newfane Flea Market was a hugely popular weekend event and a major destination for locals and tourists alike. The Market was postponed in 2020 as a result of the Covid-19 pandemic but has now reopened under new management. The market hosts a wide array of vendors including: Vintage and Antique Resellers, Crafters and Makers, Farmers, Bakers and Food vendors.

  • Wilmington Flea Market (Wilmington, VT)

Hiking + Outdoor Centers:

  • TIP! Burrows Specialized Sports (Brattleboro, VT) – Sports Rentals! Call first to inquire.

  • Black Mountain (Dummerston, VT)

  • Grafton Trails & Outdoor Center (Grafton, VT) – Truly a Vermont winter wonderland and worth the 45 minute drive North – with cross-country skiing, snowshoeing, sleigh rides, fat tire biking, hiking, swimming, and snow tubing. Ski/Snowshoe Rentals available + Lessons. Nearby you’ll find excellent dining options at Phelbs Barn Pub or MKT: Grafton. 

  • Guilford Fairgrounds (Adjacent to the Weatherhead Hollow Farmstead in Guilford, VT) – Located a two minute walk just a field and woods away, you’ll find a brand new tennis court and basketball hoops. The Fair operates once a year over Labor Day Weekend. Otherwise the fairgrounds are typically empty with occasional use by the local community. You are welcome to walk your dogs on leash or take a stroll – it's a pretty spot with a stream that our pup loves to play in.

  • Living Memorial Park (Brattleboro, VT) – Indoor ice skating rink, Ski Hill, Swimming Pool, Tennis/Volleyball Courts, and Dog Park.

  • Putney Mountain Trails – (Putney, VT)

  • Sweet Pond State Park (Guilford, VT) – an easy 45 minute loop hike around a pretty pond. About a 10 minute drive down the road. Perfect for off-leash dog hiking. The etiquette here is that if you encounter another hiker on the path, you should always call your dog to your side and allow the hiker to pass.

  • Vermont Canoe Touring Center (Brattleboro, VT) – Located at the convergence of the West and Connecticut Rivers, they provide rentals of canoes, kayaks, and paddleboards. 

  • Wantastiquet Mountain Trail (Located just over the river from Brattleboro, VT in New Hampshire)

  • Zoar Outdoor Adventure Resort (Charlemont, MA) – It's about 40 minutes South from the farmstead, and offers badass zip lining, white water rafting, and kayaking.

Movie Theaters:

Music:

Running Paths:

  • Weatherhead Hollow Road – step out your front door and run along the winding road surrounded by the hollow’s mountains on either side.

  • Keets Brook Loop – drive 5 minutes down the road to Weatherhead Hollow Pond to the parking area. You’ll find a lovely dirt road called Keets Brook located next to the parking lot that is perfect for running. It's very beautiful. There's a pretty stream that runs along the dirt road. You can run in and back or take a three mile loop by starting on Keets Brook, then in about 1 mile turn right on Simon Keets Road (you’ll go up a steep hill), and keep going until the road connects with the paved Brattleboro Road aka Weatherhead Hollow where you’ll turn right and run back down the hill on pavement to the parking area. We recommend NOT listening to music, even though the road is lightly traveled because it is a narrow winding road and you may surprise cars if you're not already aware of them. Also, the birds and wind and stream sounds are super peaceful.

Ski Resorts:

Swimming Holes:

  • West Dummerston Covered Bridge (Dummerston, VT)

  • Green River Waterfall (2435 Stage Rd, Guilford, VT) – swim under the waterfall or play with your little one or fur baby above the waterfall in the shallower water. To Park, drive through the Covered Bridge and turn left – there are clearly marked parking signs along the road (River Road). If you like to run, River Road is a beautiful dirt road and a great plan can be to run in and back out then take a refreshing dunk under the waterfall.

  • Green River Meadows (Guilford, VT) – this is located next to the Green River Waterfall mentioned above. You can run to it and back easily.

  • Indian Love Call (Newfane, VT) – popular swimming hole on the Rock River.

  • West River (Brattleboro, VT)

Theaters:

The Basics

Big-Box Stores:

  • Home Depot (Greenfield, MA and Keene, NH)

  • Target (Keene, NH)

  • Walmart (Hinsdale, NH)

Food Shopping:

  • Farm Stands:

    • Brattleboro Farmers Market

    • Franklin Family Farm (Guilford, VT) – located down the road, their self-serve farm stand offers maple syrup, fresh eggs, and frozen beef.

    • Walker Farm (Putney, VT) – a destination for flower lovers and gardeners, their farm stand carries fresh veggies and produce.

  • Grocery Stores:

    • Brattleboro Food Co-op (Brattleboro, VT)

    • Putney Food Co-op (Putney, VT)

    • Market 32 (Brattleboro, VT) – this is the closest large grocery store located at the very first traffic light off of Exit 1 off I-91.

    • Hannaford (Brattleboro, VT)

    • River Valley Co-op (330 N King Street, Northampton, MA) – located just off of I-91 near a gas station this is the place we stop if we’re coming up from NYC to avoid the extra travel time into downtown Brattleboro. They have an excellent selection of groceries including delicious to-go meals.

Hardware Store:

Health Services:

Print Services:

Pharmacy:

  • Walgreens (Brattleboro, VT)

  • Rite Aid (Brattleboro, VT)

Cafés and Restaurants

Brattleboro and its surrounding towns are home to many restaurants and pubs. While you can find excellent food here, you usually can’t find it past 9:00pm. You’ll find business hours online, but we recommend calling ahead to confirm places are open and/or making reservations.

Amy’s Bakery Arts Café (Brattleboro, VT)

A Vermont Table (Brattleboro, VT) – Featuring refined plates in a casual, welcoming environment. They search out the best Vermont artisan cheeses, hearth baked breads and highest quality meats. They take advantage of the seasons to provide fresh local herbs and vegetables from the area growers. Great craft cocktails!

Alpenglow Bistro (Wilmington, VT) – European mountain cuisine and bar in a cozy setting

Blueberry Haus (Guilford, VT) – Old Fashioned homemade ice cream within a 5 minute drive of Weatherhead Hollow.

Bruegger’s Bagels (Brattleboro, VT)

The Restaurant at Burdick’s (Walpole, NH) – Reservations are recommended at this popular French Restaurant utilizing seasonal and locally sourced foods with a menu modeled after the classic French Bistro. Located next to L.A. Burdick’s – the artisanal chocolatier (try their hot chocolate). 

Echo Restaurant & Lounge (Brattleboro, VT)

Espresso (best in town is tied among locals between these two spots):

  • Duchess Coffee – Brattleboro, VT

  • Patio Coffee – Brattleboro, VT

The Gill Tavern (Gill, MA) – The Gill Tavern celebrates the tradition and conviviality of the New England tavern, a place for the community to gather and share food and drink. This is one of our favorite restaurants.

The Gleanery (Putney, VT) – Their guiding principle is that everything that you see in The Gleanery has been carefully selected for being artisanally made. The ingredients in the dish, the dish itself, the table below it; everything is there because a person wanted to create it. They foster an environment that exalts anyone who takes pride in their craft.

The Guilford Country Store (Guilford, VT) – Only a 5 minute drive from Weatherhead Hollow, this beloved country store and café serves breakfast, lunch, and great options for dinner for eating in or taking out.

Hazel (Brattleboro, VT)

High Thai (Brattleboro, VT)

Hillside Organic Pizza (Bernardston, MA) – About a 15 minute drive South from Weatherhead Hollow, this is our favorite local pizza place.

JD McCliments Pub (Putney, VT) – Scottish Pub with live music and classic pub fare. 

Kipling’s Tavern (Brattleboro, VT) – Tasty pub fare, local Vermont Beer & classic craft cocktails served in a warm, lively atmosphere.

The Marina (Brattleboro, VT)

Mocha Joes (Brattleboro, VT)

Peter Havens Restaurant & Oyster Bar (Brattleboro, VT) – Refined New American cuisine crafted in a snug bistro setting (our fav restaurant!).

Pizzapalooza (Wilmington, VT)

The Porch Cafe + Catering (Brattleboro, VT)

Shin-La (Brattleboro, VT)

Super Fresh Organic Café (Brattleboro, VT)

Sweet Lucy’s Bakery (Bernardston, MA) – Incredible pastries and desserts. They also offer breakfast (eggs on croissant, quiche), salads, and delicious frozen pot pies that you can take home to bake for dinner.

TJ Buckleys (Brattleboro, VT)

Vermont Country Deli (Brattleboro, VT) – Gourmet-to-go marketplace, serving homemade hot and cold dishes and featuring Vermont specialty products. Try their very popular mac and cheese or variety of incredible desserts. 

Whetstone Station (Brattleboro, VT) – Informal dining - fabulous rooftop deck overlooking the Connecticut River. Variety of interesting local beer selections.

The Works Bakery Café (Brattleboro, VT)