Winter Activities Near Brattleboro

Skiing & Snowboarding

When people think of Vermont winter activities, skiing and snowboarding are usually top of mind — and for good reason. Southern Vermont has some of the most accessible mountains in New England, with options for every skill level.

Brattleboro Ski Hill

For a quick, local ski session, the Brattleboro Ski Hill at Living Memorial Park offers convenient access right in town—perfect for an after-work run or introducing kids to the sport.

Mount Snow

Just a scenic drive away (or hop on the MOOver from downtown Brattleboro!), Mount Snow delivers big mountain skiing and snowboarding, Vermont-style. Whether you’re an adrenaline junkie or a first-timer, Mount Snow has a run for you. The mountain breaks down like this: 16% beginner, 66% intermediate, and 18% advanced terrain.

Stratton Mountain

Another excellent option for downhill enthusiasts, Stratton Mountain rounds out the premier ski destinations accessible from the Brattleboro area.

Cross-Country Skiing (Nordic Skiing)

Vermont is widely considered one of the best states in the U.S. for Nordic skiing — and Southern Vermont is right at the heart of it. The region is home to deep ski history and modern trail networks that make it easy to glide through quiet forests and scenic meadows.

Retreat Trails

The Retreat Trails are a Brattleboro gem for winter recreation, offering a peaceful place for cross-country skiing close to town.

Grafton Trails & Outdoor Center

If you’re looking for a more “destination” Nordic experience, the Grafton Trails & Outdoor Center is worth the drive. With groomed trails and a cozy winter atmosphere, it’s a favorite for locals and visitors alike.

Brattleboro Outing Club

The Brattleboro Outing Club offers wonderful community-based option for people who want to enjoy winter trails and outdoor recreation without going far.

Prospect Mountain

Up for a scenic drive? Prospect Mountain’s Nordic trails are always fun — and located about 45 minutes to an hour from Brattleboro.

Snowshoeing & Winter Hiking

Not a skier? No problem. Winter hiking and snowshoeing are some of the best Southern Vermont winter activities — and a great way to explore the area at a slower pace.

• West River Trail – A gentle, scenic route perfect for all skill levels
• Retreat Trails – Multiple trail options right in town
• Grafton Trails & Outdoor Center – Well-maintained winter trails
• Hogback Mountain – Stunning views reward your winter trek

Looking for even more hiking ideas? Check out our hiking guide for additional trail recommendations.

Ice Fishing

Bundle up and drop a line through the ice at local hotspots like Retreat Meadows or the Connecticut River Setbacks. Just remember: always check ice thickness, ideally ensuring it is at least 3-4 inches for walking. Safety first means more fishing trips ahead!

Ice Skating

Few things capture the magic of winter like ice skating. Lace up your skates at:

• Retreat Meadows – Natural ice skating when conditions permit (always check ice thickness—at least 3-4 inches for walking)
• Nelson Withington Skating Facility at Living Memorial Park – A reliable indoor option
• Grafton Trails & Outdoor Center – Skating as part of their winter offerings

Snow Tubing

Snow tubing is one of the easiest ways to get outside and have a blast — no lessons required.

Mount Snow

Mount Snow’s tubing hill is located right at the base between the Main Base Lodge and the Grand Summit Resort Hotel. It’s one of the biggest in Vermont and features its own covered surface lift called the “Magic Carpet.” Ride down, hop on the lift, and repeat until your cheeks hurt from smiling.

Grafton Trails & Outdoor Center

Grafton also offers snow tubing as part of their diverse winter activity menu.

Renting Winter Gear in Brattleboro & Windham County

No gear? No problem. One of the best parts of winter in our region is how easy it is to try new things. Rental gear options include:

• Burrows Specialized Sports in downtown Brattleboro (rentals for most winter sports)
• Grafton Trails & Outdoor Center (rentals for on-site activities)
• Mount Snow (mountain rentals available)

Winter Events & Seasonal Happenings

Winter in Brattleboro isn’t just about outdoor adventure — it’s also a season full of community events and traditions.

Brattleboro Winter Farmers Market

Running every Saturday from November to March, the Winter Farmers Market is a cozy way to spend a weekend morning. Local vendors, seasonal foods, handmade goods, and the kind of friendly conversations that make Vermont feel like Vermont.

Holiday Celebrations

Southern Vermont lights up with holiday festivities. From the Brattleboro Festival of Miniatures (new as of 2025) to Last Night in Brattleboro, our annual New Year’s celebration, there are so many ways to celebrate the season.

Brattleboro Winter Carnival

An annual tradition, happening each year in February, the Brattleboro Winter Carnival skating, bonfires, and winter fun for the whole family.

Harris Hill Ski Jump

This long-standing Brattleboro tradition (since 1922!) is held on an Olympic-size, 90-meter ski jump — the only one of its kind in New England, and one of only six in the U.S. of this caliber.

The Harris Hill Ski Jumping Competition takes place every year on Presidents Day weekend and offers spectators the chance to experience the Olympic sport of ski jumping up close in all its breathtaking, heart-stopping glory.

Warm Up with Indoor Activities

Once you’ve experienced all the outdoors has to offer, warm up by visiting the many shops and restaurants in our region. From cozy cafes to unique boutiques, downtown Brattleboro and the surrounding towns offer plenty of ways to extend your winter adventure indoors. Discover all our indoor activities for a complete Vermont winter experience.