Are you itching to escape the monotony of everyday life? If you answered “yes,” then make Brattleboro your next stop when looking for fun things to do in Vermont.

Take a break from the busyness and stress of life and surround yourself with nature, quaint boutiques, and fun activities in Brattleboro, Vermont. This quaint, quiet town is a hidden gem in a rustic setting. It’s the perfect place for a romantic escape, a family vacation, or an adventurous getaway.

With countless things to do — and much of them in the great outdoors — your retreat awaits to delight you with experiences in one of New England’s best-kept secrets. But don’t take our word for it; come check it out yourself!

While scattering your travel plans across countless Vermont destinations is tempting, start and end your adventure here in Brattleboro, especially if you plan to adventure in the autumn. This vibrant town is known for its autumn splendor with breathtaking views, quaint shops, welcoming hotels, and impressive trails for all skill levels.

The atmosphere is brimming with a local charm that’s hard to find elsewhere. So, engage with the community, create some lasting memories, and, for goodness sake, don’t leave home without your camera.

Catch a Flick at the Latchis Hotel

When you’re looking for a cozy way to unwind after tackling our town’s many outdoor activities, stop at the Brattleboro, Vermont movie theatre — conveniently located in the Latchis Hotel. It’s full of old-school flair, making you wonder if time travel is possible.

The Latchis Theatre is a historical gem — a throwback to yesteryears when watching movies came not just with buttery popcorn and cola but with class. Its art deco elegance mixes new releases and nostalgic classics. So, indulge your inner film buff and soak up some cinematic history. Grab that oversized tub of popcorn and snuggle down into a vintage seat for a great flick and an experience you won’t forget.

Shop ‘Til You Drop for Fall Finds

Forget the cookie-cutter malls or big box stores common to city life. Brattleboro stores have you covered with a fun and quirky retail scene that’s as delightful as our town. Out here, you’ll dive into a treasure trove of boutique shops where contemporary palates bump elbows with the eclectic and vintage, such as:

So, if you’re looking for the perfect pumpkin-spice sweater, a contemporary new kitchen tool or art, or an eclectic retro find that screams, “I’ve got style,” our boutiques will keep you shopping all autumn long. So grab your reusable shopping bags, book your room for the weekend — or the whole week — and get ready to satisfy your retail therapy craving.

A Must-Visit Fall Festival

Brattleboro, Vermont, attractions and festivals are unlike those elsewhere. Take our Fermentation Festival, for instance. Where else will you find giant pickles on parade — and a celebration of all things fermented?

Our fermentation festival, which happens in early September, features everything from pickles to kimchi and miso to cider. We’re ‘down’ with live music, workshops, and more. It’s an excellent time for the entire family.

Brattleboro Trails to Brag About This Fall

They don’t call Vermont the “Green Mountain State” for nothing. Not only is our quaint town surrounded by the Green Mountains, but we also love exploring them, and so do our many visitors. So, there are lots of local trails to hike or bike — eleven Vermont state park trails, to be exact. And you’ll find trails for every skill level — beginner through advanced.

Some of our trails are as old as the hills (really!). Many Retreat trails are over 100 years old but are well-graded for easy walking or mountain biking and stretch for 11 miles.

If you’re looking for a short, easy hike, Fort Dummer State Park is an excellent choice, with the 0.9-mile Sunrise trail and the half-mile Sunset trail to explore.

Moderately skilled hikers like the Living Memorial Part trails, which have a one-mile loop and include a section of the road. If you’re up for the challenge of a more advanced and adventurous trail, then Wantastiquet Mountain is the place for you. But fair warning — the trails are unmarked, with a moderate to difficult climb to the summit and with switchbacks. So, this is not a hike for beginners.

Your Perfect Fall Getaway Awaits You in Brattleboro

So, what are you waiting for? Step away from the stress of life’s hustle and bustle and enjoy some fun things to do in Vermont.

Embrace the charm of small-town life right here in Brattleboro this fall. Reconnect with nature, unwind, and enjoy the gorgeous autumn splendor. Book your perfect fall getaway today.