5 Fall Itineraries: Things to Do in Brattleboro Vermont

Between the cozy sweater weather and colorful arrays of leaves stretching as far as the eye can see, this southern Vermont town has plenty to brag about. But what exactly should you include in your Brattleboro fall itinerary? No matter how long your visit is, there are plenty of things to do in Brattleboro, Vermont between shopping, dining, and immersing yourself in the town’s quirky charm.

Things to do in Brattleboro, Vermont includes seeing it from the top of Mt. Wantastiquet.
Photo: Wikimedia Commons

Things to do in Brattleboro, Vermont:

One Day

Just passing through? No problem. Here are some things to do in Brattleboro for your one-day stay:

  • Breakfast: Warm up your morning with a hot cup of coffee and a breakfast sandwich in one of the cozy cowhide seats at The Works.
  • Late morning: Take a walk in our vibrant downtown and historic district. Look out for artistic highlights hidden in plain sight (on our list: the Carter’s Little Liver Pills sign).
  • Lunch: Grab a bite at the aptly-named and very delicious Brattleburger. Grab a seat towards the back for the best view.
  • Afternoon: Take a hike up Mt. Wantastiquet, just across the New Hampshire border, and get a top-notch view of Brattleboro.
  • Dinner: Wind down at Whetstone Station, with dinner in a fire-lit dining room and an outdoor craft beer bar with an unforgettable view.

Three Days

Your weekend in Brattleboro can be about more than just leaf-peeping — here are two more itineraries to add to your stay.

  • Breakfast: Enjoy some speciality coffee and Belgian-style waffles at The Restless Rooster.
  • Late morning: Seek out fresh local fare at the Brattleboro Farmer’s Market.
  • Lunch: While you’re weaving through the stands at the market, why not grab some lunch on the go? There’s nothing like a hot lunch on a breezy day!
  • Afternoon: Meet some goats and conquer a (sometimes haunted) corn maze at Gaines Farm in Guilford.
  • Dinner: Treat yourself to some locally-sourced steak or pasta at the New England House.
  • Breakfast: Have a savory omelet at The Porch Too — and for the sake of fall, an apple cider doughnut!
  • Late morning: Hunt for those perfect red and heirloom apples to take home at the Scott Farm Orchard.
  • Lunch: Head over to the Chelsea Royal Diner for some good ol’ home-style fries!
  • Afternoon: Stop by the Vermont Center for Photography to see work by some of the finest photographers in the region.
  • Dinner: Dig into savory and creative meal brimming with local ingredients at the whimsical Duo Restaurant.

Five Days

If you’re dedicating that full vacation to southern Vermont, don’t fret about whether or not you can fill up your week — there’s more than enough activities to keep you busy. Here are two more days to add to your trip.

See Brattleboro's Fall Colors

With a mountainous backdrop and more than enough options to eat, shop, and explore, Brattleboro makes a perfect fall destination. The folks at the Latchis Hotel are ready to help you plan your autumn Brattleboro visit.

Mt Wantastiquet Panorama during fall foliage