Top Things to See in Brattleboro VT: Culture, Nature, Dining, and More

In the heart of southern Vermont lies a hidden gem that effortlessly blends culture, nature, and community spirit. From its vibrant downtown area teeming with unique shops and delectable eateries to the picturesque trails and serene waterways that surround the town, Brattleboro offers a delightful array of experiences. It’s a place where the arts thrive, outdoor adventures beckon, and a warm, welcoming atmosphere embraces every visitor.

Walking through the downtown streets, you’ll find an eclectic mix of restaurants, galleries, and boutiques. The town’s lively arts scene comes alive with monthly gallery walks, local theater performances, and musical events that showcase the rich cultural fabric of Brattleboro. Whether you’re indulging in the local cuisine at one of the many fine dining establishments or exploring the quaint shops, there’s always something new and exciting to discover.

For those who seek outdoor activities, Brattleboro is a paradise. The nearby trails offer everything from leisurely strolls to challenging hikes with breathtaking views. Water enthusiasts can enjoy kayaking, canoeing, and tubing on the tranquil rivers, while winter visitors are just a short drive from some of New England’s top ski resorts. No matter the season, Brattleboro provides a captivating blend of adventure, relaxation, and charm that leaves a lasting impression on all who visit.

Exploring Downtown Brattleboro

Brattleboro | Vermont Tourism

Walking Through Downtown

One of the first things you’ll notice about Brattleboro is its walkability. Staying at the Inn on Putney Road B&B, I found it incredibly convenient to stroll a few blocks into downtown. The route takes you past a lovely park and brings you into the heart of the town where you can explore:

  • Restaurants: Downtown Brattleboro is a culinary delight with a variety of restaurants. Whether you’re craving farm-to-table cuisine, ethnic foods, or just a good old burger, you’ll find it here.
  • Shops: The unique shops offer everything from books to sporting goods, and there are plenty of opportunities to pick up a special souvenir or gift.
  • Galleries and Pubs: Art lovers will appreciate the many galleries, while those looking to unwind can enjoy a drink at one of the cozy pubs.

Cultural Events and Festivals

Brattleboro is alive with music and festivals. Throughout the year, the town hosts numerous events that bring the community together and welcome visitors with open arms.

  • Music Events: Live music is a staple in Brattleboro, with performances happening regularly in various venues around town.
  • Festivals: The town celebrates numerous festivals, each offering a unique glimpse into the local culture. From parades to seasonal celebrations, there’s always something happening.

Shopping and Dining

Visit Downtown Brattleboro: Main Street & Beyond | Happy Vermont

Shopping Extravaganza

If you love to shop, Brattleboro won’t disappoint. The downtown area is dotted with a variety of stores that cater to different tastes and interests.

  • Main Street Stores: Walk along Main Street and you’ll discover an array of shops selling everything from handcrafted goods to high-end outdoor gear.
  • Unique Finds: Off Main Street, the smaller shops offer unique items that you won’t find anywhere else. It’s a shopper’s paradise where you can spend hours exploring.

Culinary Delights

The dining scene in Brattleboro is vibrant and diverse. With over 30 restaurants and pubs, there’s something to satisfy every palate.

  • Local Eateries: The town prides itself on its local eateries that offer fresh, delicious meals. Many of the restaurants source their ingredients from local farms, ensuring a farm-to-table experience.
  • International Cuisine: If you’re in the mood for something different, there are plenty of international cuisine options to choose from. Whether it’s Thai, Italian, or Indian, you’ll find it here.

Outdoor Activities

Top 12 Hikes and Walks around Brattleboro | Komoot

Hiking Adventures

Brattleboro’s natural beauty is best explored on foot. There are numerous hiking trails in and around the town, each offering a unique experience.

  • Retreat Trails: For a leisurely stroll, the Retreat Trails are perfect. These trails offer scenic views and a peaceful environment, ideal for a relaxing hike.
  • Mount Wantastiquet: For those looking for a more challenging hike, Mount Wantastiquet provides a rewarding trek with stunning vistas at the top.
  • Mt. Monadnock: A short drive away, Mt. Monadnock is known as the most climbed mountain in the world. It’s a must-visit for the truly adventurous.

Biking Routes

Brattleboro is also a great destination for biking enthusiasts. The town offers bike routes for all levels, from beginners to seasoned cyclists.

  • Scenic Routes: The bike routes take you through a variety of settings, from peaceful countryside to challenging hills.
  • Multi-State Trip: One of the most exciting routes takes you on a trip through three New England states, offering a unique and memorable biking experience.

Water Activities

Given Brattleboro’s proximity to the water, there are plenty of opportunities for water-based activities.

  • Kayaking and Canoeing: The town’s location on the water makes it an ideal spot for kayaking and canoeing. There are rental shops nearby where you can get all the equipment you need for a day on the water.
  • Tubing: For a more relaxed experience, tubing is a fun way to spend a sunny afternoon. Just float down the river and enjoy the scenery.

Skiing in New England

During the winter months, Brattleboro becomes a hub for skiing enthusiasts. The town is conveniently located near several major ski areas.

  • Nearby Ski Resorts: Within a 45-minute drive, you can reach ski resorts like Mt. Snow, Stratton, Bromley, Magic Mountain, and Okemo. Whether you’re a beginner or an expert, there’s a slope for you.

Art and Theater

Gallery Walk - Brattleboro Vermont

Gallery Walk

Art lovers will be thrilled with Brattleboro’s vibrant art scene. The First Friday of every month is dedicated to the Gallery Walk, an evening where galleries open their doors to the public.

  • Open Houses: The Gallery Walk is an opportunity to explore local art, meet artists, and enjoy the creative atmosphere of the town.
  • Art Exhibits: Many of the galleries feature rotating exhibits, ensuring that there’s always something new to see.

Theater Performances

Brattleboro is home to a number of theaters that offer a range of performances.

  • Live Theater: Venues like NEYT and the Hooker-Dunham Theater showcase local talent with live theater performances.
  • Movie Theater: The Latchis Theater, a restored Art Deco movie theater, is a great place to catch a film in a historic setting.

Farmers Market

At the Brattleboro Farmers' Market | ericafterschool

Saturday Market

The Brattleboro Farmers Market is a must-visit. Held every Saturday during the warmer months, it’s a great spot to pick up fresh, local produce and handmade goods.

  • Fresh Food: The market offers a variety of fresh fruits, vegetables, and other farm products. It’s the perfect place to stock up on healthy, delicious food.
  • Lunch Options: Many vendors offer prepared foods, making it a great place to grab lunch and enjoy it in the outdoor market setting.

Winter Market

During the winter months, the Farmers Market continues on a monthly basis.

  • Seasonal Goods: Even in the colder months, the market features seasonal goods and festive items, providing a year-round market experience.

Nearby Colleges

Tour college: Landmark College

Brattleboro is home to several educational institutions, making it a great place for visitors with academic connections.

  • Marlboro College: Known for its liberal arts programs, Marlboro College is a prominent institution in the area.
  • Landmark College: Specializing in education for students with learning differences, Landmark College is another key institution.
  • School for International Training: Offering graduate programs and study abroad opportunities, the School for International Training adds to Brattleboro’s academic appeal.


Brattleboro, Vermont is a town that offers a rich tapestry of experiences. Whether you’re here for the arts, the outdoor adventures, the food, or just to soak in the local culture, you’ll find plenty to see and do. It’s a place that welcomes you warmly and leaves a lasting impression. My visit to Brattleboro was filled with wonderful memories, and I’m sure yours will be too.