Things to Do in Brattleboro, VT

By VI | Disclosure: I use affiliate links

Dining with a view of the river in the summer

Courtesy of Christian Hinkle - Fotolia.com

I’ve always found Brattleboro, Vermont to be one of those places that just feels good—no matter the season. If you’re anything like me and love to explore on foot (or on snowshoes in the winter!), you’ll fall for this Southern Vermont gem nestled along the Connecticut River. Brattleboro has something for everyone—whether you're hitting the slopes in winter or biking through leafy trails in summer. And the art scene? I never miss a stop at the Brattleboro Museum & Art Center when I’m in town.

Brattleboro, VT Highlights:

For Families: Visit the Retreat Farm – I’ve walked the farm trails and met the animals—it’s perfect for kids and grown-ups alike.
For Outdoor Enthusiasts: Hike to the top of Mount Wantastiquet – I’ve made the climb, and the view over Brattleboro is always worth it. You’ll love the challenge and the reward.
For Kids: Explore the Brattleboro Museum & Art Center – I was surprised how much the little ones enjoyed the interactive exhibits. You’ll find something creative for every age.
For an Adventure: Paddle or float the Connecticut River – I’ve paddled on a warm summer day and felt totally at peace. If you like river time, you’ll want to try this.
For Shoppers: Browse downtown bookstores, artisan shops, and galleries – I always find a new treasure when I stroll downtown. You’ll love the quirky shops and friendly vibe.

Best Time to Visit Brattleboro, VT

From my experience, the sweet spot is fall (September–October)—I’ve never seen foliage like it, and the festivals are so much fun. But if you prefer warm days and outdoor markets, you’ll love summer (June–August) too. I’ve spent many weekends here enjoying concerts, riverside walks, and fresh produce from the farmers market.

How to Get to Brattleboro, VT

If you are traveling by car: I usually drive in on I-91—it’s an easy and scenic trip, just 2 hours from Boston or about 3.5 from NYC.
By Train: I’ve taken Amtrak’s Vermonter and stepped off right downtown. You’ll love the relaxed pace and beautiful views on the way.
By Air: I’ve flown into Bradley (CT) and Manchester (NH); both airports are about 1.5–2 hours from town and make a good starting point for your getaway.

Where to Stay in Brattleboro, VT

Latchis Hotel – I stayed here once and loved the mix of vintage charm and downtown convenience. Bonus: there’s a movie theater downstairs!
The Inn on Putney Road – This B&B was a peaceful escape for me. You’ll love the gardens, gourmet breakfasts, and riverside setting.
Colonial Motel & Spa – When I needed something affordable and easy, this spot checked all the boxes. Plus it has an indoor pool for relaxing after a hike.