Brattleboro Vermont with Kids: The Best Things to Do, Restaurants and Hotels

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By - By Anna Fader

We've been vacationing in Southern Vermont since before we had kids, thanks to a relative with a lovely house in Wilmington. On every visit, we gravitate to Brattleboro when we need to get out of the house. Brattleboro, Vermont is a charming old New England small town with just a hint of Vermont funkiness. There are plenty of good restaurants and lots of things to do to keep the entire family occupied.  

Below is my personal list of things to do in and around Brattleboro with kids, which I pull out whenever just enjoying the fresh mountain air and playing with sticks gets old. I've included a few of the most interesting places to stay (although I've never stayed in any of them myself) and the best restaurants for families in Brattleboro to round out the list with everything you need to know to make Brattleboro a perfect family vacation destination for a weekend or a week, any time of year.   

  1. Visit a family run farm and buy maple syrup from the source at Robb’s Family Farm.
  2. Pick your own apples, peaches, and plums at Cortland Hill Orchard (mid-August to mid-November).
  3. Feed and touch over 50 animals at Retreat Petting Farm (Seasonal).
  4. Buy local produce and crafts in a festive atmosphere at the Brattleboro Farmers Market (Wednesdays and Saturdays, May through October).
  5. Take a sleigh or wagon ride at Fair-Winds Farm, an actual working horse-drawn farm.
  6. Take a hike or pitch a tent at Fort Dummer State Park.
  7. Let the kids munch on free popcorn while you shop for shoes, clothes or gear at Sam’s Outdoor Outfitters.
  8. Let the kids go wild with creative and imaginative play at indoor Kidsplayce.
  9. Take a reading break at the Brooks Memorial Library Children’s Room.
  10. Keep your fun out of the gutter at Brattleboro Bowl.
  11. Splash in the summer or skate in the winter at Living Memorial Park.
  12. Take an easy hike to climb the fire tower at the top of Mt Olga in Molly Stark State Park.
  13. Swim in the West River under the historic Dummerston covered bridge.
  14. Catch a show staged by the New England Youth Theatre.
  15. Go swimming in Lake Whitingham.
  16. Go for a nighttime bonfire and wagon ride or a winter sleigh ride at Adams Family Farm in nearby Wilmington.
  17. Pick your own berries, pumpkins or flowers (depending on the season) at Boyd Family Farm in Wilmington.
  18. Challenge yourself with the aerial course, the alpine slide or just enjoy the rides at Bromley Adventure Park (I hour north).
  19. Take a themed historic train ride on the Green Mountain Railroad from White River Junction.
  20. Go downhill skiing at Mt Snow.
  21. Time travel through 3 floors of eclectic antiques at Twice Upon a Time.
  22. See the Vermont’s wildlife in the form of 600 taxidermied animals (and a few live ones) at the Southern Vermont Natural History Museum in nearby Marlboro.
  23. Visit the stunning Chesterfield Gorge.
  24. Pick your own berries at High Hopes Farm in nearby Westmoreland, NH.
  25. Play dress up and explore the charming works of illustrator Tasha Tudor in her tiny museum.
  26. Grab some bargain second-hand kids clothing, toys or gear at Whippersnappers.
  27. Play the coin-operated skeeball game hidden amongst a nice selection of reasonably priced toys at the back of Beadniks.

    Brattleboro Annual Events

  28. Moo along at the Strolling of the Heifers annual parade and celebration (early June).
  29. Beat back the winter blues at the Brattleboro Winter Carnival (mid-February).
  30. Make and fly kites and celebrate Asian cultures at the Children’s Day Brattleboro Kite Festival of Japan, China and India (May)
  31. Catch Circus Smirkus’s arrival in town for amazing teenage performances (July).

    Brattleboro Restaurants

  32. Pick up picnic fixings at Carol’s Main St Cafe.
  33. Eat on the outdoor decks of The Marina restaurant.
  34. Stop in for a sandwich, snack or a scoop at Amy’s Bakery Arts Cafe.
  35. Nosh on delicious ethnic food at India Palace.
  36. Pick up local foods at the Brattleboro Food Co-op.

    Brattleboro Hotels

  37. Enjoy the cozy charm and indoor saltwater pool at the Colonial Motel.
  38. Wake up to llamas and chickens at Spirit HIll Farm Bed & Breakfast.
  39. Stay right in downtown Brattleboro’s historic Art Deco hotel, The Latchis.
  40. Sleep in Rudyard Kiplings house, Naulakha, where he wrote The Jungle Book and Captains Courageous.