Gallery Walk

Brattleboro Kayak and Canoe
451 Putney Road
Brattleboro, VT 05301-9183
(802) 257-5008

Brattleboro Literary Festival

Brattleboro Museum & Art Center

The Retreat Farm

Farmers Market

Green Mountain Orchard

Grafton Cheese Company

Kids Playce
(creative indoor play space)
20 Elliot Street
Brattleboro, VT 05301-3216
(802) 254-5212

Hike Mt. Wantastiquet

Environmental Education Center

Downtown Shopping

Outlet Shopping

Movie Theater



Amy's Bakery Arts Cafe

Fireworks Pizza

Top of the Hill Grill

The Marina

Brattleboro Food Coop

The Shin-La
57 Main Street
Brattleboro, VT 05301-3257
(802) 257-5226

Whetstone Station

Fall Open House, Saturday, October 5th 2013 from 11am-1pm

October is foliage season in New England! Here’s what's happening in beautiful Brattleboro and the surrounding area the first weekend in October.

36 Hours in Brattleboro, Vermont
Appearing in many national magazine's  "Best Small Towns" top ten  lists, Brattleboro, Vermont offers visitors the experience of a quaint New England town with a hip, progressive edge, nestled within the beautiful Green Mountains. We hope you find this itinerary helpful in getting the most out of your visit.


After you cross the state line on I-91, stop by our award-winning Vermont Welcome Center. Kids can pretend to ride in an old gondola, learn a bit about the state, and maybe even sample some cheese or maple syrup.

Grab a pick-me-up at our Brattleboro Food Coop. This independent whole foods store offers locally grown and made products and a cafe area complete with kids' play space and mountain view.

Enjoy free admission to over 30 galleries open to the public at Brattleboro's monthly Gallery Walk. While you're there, grab a bite at one of our many family-friendly downtown restaurants. Fireworks is an excellent choice for pizza or pasta lovers.

Savor dessert and play a game of checkers or chess at Mocha Joe's before catching a movie at our historic Latchis Theater.


Grab a light break breakfast at the Vermont Country Deli or save your appetite and continue on to The Farmer's Market 500 yards down the road--a weekly affair that includes music, a sandbox, produce, hot food, and local wares.

Time for the Oak Meadow Open House. Meet your teachers, view curriculum, make arts and crafts, and participate in a homeschooling Q+A!

Head to lunch at any of our favorite downtown sandwich shops. Staff favorite include Amy's Bakery Arts Cafe, The Works and The Humble Kitchen.

Writer's Circle named the Brattleboro Literary Festival one of the top five upcoming Writing and Literary Festivals in the U.S.! The four-day festival includes readings, panel discussions, and special events, featuring emerging and established authors. Free and open to the public!

Visit our local favorite, Top Of The Hill Grill, for take out or outdoor dining. You'll love their authentic pit bar-b-que, homemade sides & salads, vegetarian selections, and homemade desserts.

Worn out from a busy day? If you're staying at our local Holiday Inn Express or Colonial Motel, you can relax while your kids enjoy swimming in their indoor pools.


Enjoy brunch and fabulous views at The Marina, on Putney Road. You can cross the street and rent a canoe or kayak at The Vermont Touring Center and paddle the Connecticut or West Rivers.

Head out for some apple picking (check out Green Mountain Orchards) or a kid friendly hike up Black Mountain. Or, walk the Retreat Trails and end with a visit to to The Retreat Farm and Grafton Village Cheese where the kids can sample Vermont's own Grafton cheddar.



Oak Meadow Office
74 Cotton Mill Hill 2nd Floor, Brattleboro, VT

From I-91 north or south take Exit 2, Brattleboro/VT-9E. Follow Western Avenue/9E, bear left at intersection, where Western Avenue turns into High Street. At bottom of High Street turn right onto Main Street. Go through 2 sets of lights and bear right up hill and take first left which is South Main Street. Follow South Main until stop sign. Turn left onto Cotton Mill Hill. Oak Meadow is in the mill building on your left down the hill. Follow the Oak Meadow signs for the office.

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Colonial Motel Spa
889 Putney Road
Brattleboro, Vermont 05301

Holiday Inn Express
100 Chickering Drive
Brattleboro, Vermont 05301

Latchis Hotel
50 Main Street
Brattleboro, Vermont 05301

1868 Crosby House B&B
175 Western Avenue
Brattleboro, Vermont 05301

Things To Do In Areas Surrounding Brattleboro:


Science Museum


Green Mountain Railroad

The Eric Carle Museum

October 7 Harvest Festival
Open to the public. No admission fee.

25th Annual Medieval Fair
The Grammar School
69 Hickory Ridge Road South
Putney, Vermont

Highlights: Merlin the Wizard, climbing walls, archery, candy-throwing catapult, haunted dungeon, dunking booth, pony rides, slay-the-dragon pinata, scavenger hunts, knightings by King Arthur himself!

Admission is FREE. Individual game and ride passes are available with proceeds benefiting the student scholarship fund at The Grammar School.



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