Winter in New England is one of the most picturesque seasons, with plenty to explore from snow-covered villages and quiet mountain roads to thrilling outdoor adventures and cozy evenings in by the fire. The region offers an impressive variety of things to do in New England once the temperatures drop. While fall and summer might be the more traditional travel seasons for this area, unless you’re an avid skier, we’re here to show you that there is more to do than just hitting the slopes!
For those planning Northeast winter vacations, as the snow blankets Vermont, the landscape takes on a peaceful atmosphere. The village of Brattleboro is an ideal base for discovering these seasonal highlights. Located in southern Vermont, near the borders of New Hampshire and Massachusetts, it places visitors close to classic winter activities while still offering dining, shopping, and cultural attractions.
One of the best things to do in New England is exploring the small lodging properties and Bed and Breakfasts that pepper the back roads. It’s the easiest way to make your winter getaway more memorable than all the rest! If you prefer staying at boutique hotels in Brattleboro, VT, one of the best places to enjoy a weekend getaway in New England is at Inn on Putney Road. Enjoy charming guest rooms, a home-cooked breakfast each morning, and so much more. We can’t wait to host you; book your lodging today!
The Best Things to Do in New England this Winter near Brattleboro
Winter travel is especially rewarding when days are filled with exciting outings and evenings are spent unwinding. From snowy trails to historic villages, the following experiences are all right in town or within an hour of Brattleboro and showcase some of the most enjoyable things to do in Vermont and the surrounding region during winter.
With Valentine’s Day just around the corner, many of the best things to do in New England are ideal for couples’ retreats and romantic getaways in Vermont!
Best Things to Do in New England This Winter Near Brattleboro:
- Located less than 30 minutes from Brattleboro, Mount Snow is one of the most popular winter destinations in southern Vermont. Skiing and snowboarding are the main draws, but the mountain also offers snowshoeing, tubing, and scenic gondola rides. Even non-skiers enjoy the lively base area and winter views.
- Downtown Brattleboro is full of character year-round, but in winter it takes on a quieter charm. Browse local bookstores, art galleries, and specialty shops, then warm up in one of the town’s cafes or restaurants. This area is central to many things to do in Brattleboro VT and is perfect for a relaxed afternoon.
- The Retreat Trails system offers miles of wooded paths just minutes from downtown Brattleboro. In winter, these trails are ideal for snowshoeing or cross-country skiing. It is an easy way to enjoy the outdoors without committing to a full-day trip. These thrilling outdoor cold-weather activities are one of the best things to do in New England in the winter!
- The Harris Hill Ski Jump in Brattleboro, Vermont, is a historic ski jumping venue featuring an Olympic-size 90-meter hill where world-class jumpers compete each year in a long-running two-day tournament that has been a local tradition since 1922. By far, one of the unique things to do in New England during your winter getaway.
- About 45 minutes north of Brattleboro, Chester is a picturesque village with stone architecture and classic New England charm. Winter is a great time to stroll the village green, explore antique shops, and enjoy a leisurely lunch in a historic setting.
- For those who enjoy hiking year-round, Wantastiquet Mountain offers trails with views of the Connecticut River Valley. Located just across the river in New Hampshire, it is a popular local hike and one of the lesser-known winter outdoor experiences near Brattleboro.
- Discover Art and History at the Brattleboro Museum and Art Center. This contemporary museum showcases rotating exhibitions that feature regional and national artists. Winter is an ideal time to explore indoor attractions like this, especially on colder days when you want culture without braving the elements for long periods.
- Plan to take in a show at the Vermont Jazz Center. It’s an excellent creative space to hear some of the up-and-coming talent, as well as long-time performers who love sharing their craft with audiences.
One of the Most Romantic Boutique Hotels in Brattleboro, VT
Choosing the right lodging plays a big role in creating memorable weekend getaways in New England. For those looking for a more intimate experience, boutique hotels in Brattleboro, VT, are small, locally owned establishments with dedicated Innkeepers on hand to create the best winter getaway. Staying close to downtown and major attractions allows you to spend more time enjoying winter activities and relaxing!
The Inn on Putney Road offers a refined yet welcoming option for winter travelers. Our location provides easy access to the best things to do in New England during the colder months, from skiing at Mount Snow to exploring downtown Brattleboro. Guests appreciate returning from a day outdoors to a warm, inviting space that feels personal rather than generic. Spacious guest rooms, thoughtful amenities, breakfast each morning, and attentive hospitality make it a natural choice for Northeast winter vacations.
Winter stays at one of the best boutique hotels in Brattleboro, VT, are especially appealing for couples and adults seeking a quieter escape. Whether you are planning a short weekend or a longer seasonal escape, our Inn offers a comfortable home base for discovering the best of southern Vermont in winter. Join us this winter in Brattleboro; book your lodging today!
