A winter scene featuring Greenberg Headwaters Park in Bennington, Vermont

You already know that winter is a special season in Vermont, but did you know that Bennington is a mecca for winter recreation? Not only is Bennington within 30 miles of several major ski resorts, but there are numerous trails for snowshoeing, cross-country skiing, and winter hiking.

In Bennington, there’s no need to escape winter. Embrace it with these great opportunities for recreation, inside and out. 

*We’ve categorized the trails that are best for a few different types of recreational activities, but there’s definitely overlap. No snow? Most of the spots are also awesome for a winter hike.

Great Places for Cross-Country Skiing in Bennington

Cross-country skiing is a fabulous sport for all levels of fitness, and the topography of Bennington makes it an awesome spot for scenic ski trails. Here are some of our favorite spots for cross-country skiing.

Prospect Mountain, Woodford, VT

Cross-country skiers at Prospect Mountain in Woodford VT
Young skiers at Prospect Mountain in Woodford. Photo credit: Prospect Mountain

With more than 30 kilometers of groomed trails for skiers of every skill level, Prospect Mountain is one of the best nordic ski centers in the state of Vermont. Located just eight miles from downtown Bennington, Prospect’s high elevation means that it often gets snow when the valley is dry.

 If you’ve never skied before, the trails at Prospect Mountain make learning easy. You can rent skis for the day and take a lesson with a local expert. You’ll be hooked in no time. 

Woodford State Park, Woodford, VT

Cross-country skiing in Woodford State Park, Vermont.
Cross-country skiing in Woodford State Park

Woodford State Park is located just up the road from Prospect Mountain. The park officially closes in October, but winter enthusiasts are welcome to park outside the gates to take advantage of the trails. 

The best place to cross-country ski in Woodford State Park is on the unplowed campground roads or right on Adams Reservoir when it freezes over. There is also a 2.7-mile hiking trail that circles the lake, but this is a narrow, rocky trail and best suited for snowshoes or winter hiking. 

Woodford State Park sits at 2,400 feet above sea level, so you will usually find snow all winter and into the spring.

Mile-Around Woods, North Bennington, Vermont

Located adjacent to the Historic Park McCullough House in North Bennington, the Mile-Around Woods is a series of walking trails through field and forest with magnificent views of the nearby farms, valleys, and mountains.

The original carriage road was built after the Civil War by Trenor Park, whose goal was to create a circular path exactly a mile in length without cutting down a single tree. The trails now total more than six miles and are managed by the Fund for North Bennington.

You can ski the original Mile-Around path through an old hardwood forest, or you can meander through the snowy fields. Either way, the Mile-Around trails make for excellent skiing, snowshoeing, and winter hiking.

Greenberg Headwaters Park, Bennington, Vermont

Sunset over the wetlands in Greenberg Headwaters park in Bennington.
Sunset over the wetlands in Greenberg Headwaters Park

Located in downtown Bennington, Greenberg Headwaters Park consists of 168 acres of upland forest and wetlands, as well as beautiful portions of the Walloomsac River, Jewett Brook, and South Stream. A well-maintained network of trails makes this a lovely spot for a peaceful ski.

There are a few different parking/access points for the Greenberg Preserve, but for cross-country skiing, the best trails should be accessed off of Belvedere Street, which is a short, dead-end street off of Morgan Street. The trails on the west side of the footbridge are wide and easy to maneuver, traveling through a lovely meadow and along the river, with great views of the expansive wetlands.

Greenberg Headwaters Park is also a nice spot for snowshoeing, fat biking, and watching wildlife.

Where to Snowshoe in Bennington

These are trails that may not be suitable for skis, but are perfect for snowshoes or microspikes. 

Lake Shaftsbury State Park, Shaftsbury, Vermont

Snowshoeing in Lake Shaftsbury State Park
Snowshoeing in Lake Shaftsbury State Park

The trail around Lake Shaftsbury is exactly a mile, and is perfect for novice snowshoers, as there are very few steep sections. During the winter when the park is closed, you will have to park outside the gate and walk along the beach to the trail. Traveling clockwise, the trail heads into a mixed hardwood forest and then descends into a small wetland on a boardwalk. This is a great spot to look for winter birds.

After meandering through the wetland, the trail climbs into a dense hemlock forest along a ridge with great views of the lake below. On this side of the lake, you will cross two footbridges, followed by two vacation homes, before popping out onto the state park road where you left your car. The whole walk can be completed in under 45 minutes. 

Bald Mountain Trail, Bennington, Vermont

The Bald Mountain hike is more of a challenge due to its length and steepness, but it’s an exhilarating trek for intermediate and advanced snowshoers that totals about 5.6 miles. There is quite a bit of elevation gain, so expect the snow to get deeper as you climb. You’ll find ample parking at the trailhead on North Branch Street.  

Bald Mountain trail starts by climbing through dense brush along a power line as you make your way to the self-proclaimed “tunnel of self-expression” that goes under the highway. After the tunnel, the trail follows an old logging road into the Glastenbury Wilderness. The White Rocks vista is a great spot for a hot chocolate break before turning around and heading back to the parking area. 

Robert Frost Trail, North Bennington, Vermont

The Robert Frost Stone House Museum in winter
The Robert Frost Stone House Museum in winter

You can begin your snowshoe adventure on the Robert Frost Trail at the Robert Frost Stone House Museum in Bennington or at the Lake Paran beach in North Bennington. This 2-mile (one-way) trail travels through dense woods, along the edge of farm fields, across Paran Creek, and along a beautiful upland meadow with fabulous views of Lake Paran.

The Robert Frost Trail is pretty easy with a few moderate inclines, so it’s perfect for novice snowshoers and families with kids. 

Bennington Area Trail System, Bennington, Vermont

BATS stands for Bennington Area Trail System. As a non-profit 501 (c)(3), BATS works with public and private landowners to plan, build, and maintain trails for sustainable, non-motorized use in and around the Bennington, Vermont area. The organization was founded by a group of local bikers, runners, and hikers that advocate for multi-use singletrack trails for the enjoyment of area residents and visitors alike.

BATS is currently made up of a vast network of multi-use trails on the side of Mount Anthony near the former Southern Vermont College. Use the trail map to find a trail suitable to your level of expertise. There are trails for all levels snowshoeing, as well as winter hiking and cross-country skiing.

Indoor Recreation in Bennington

If you’d rather work up a sweat indoors, you’ve got a few options right in Bennington.

Bennington Recreation Center, Bennington, Vermont

Located on Gage Street, the Bennington Recreation Center features a full size pool for laps, a fitness and strength-training room, and a small sauna in both the men’s and women’s locker rooms. In 2019, the Bennington Recreation Center partnered with the Berkshire Family YMCA to offer expanded equipment and programming.

Stop into the Bennington Rec Center to take advantage of the weight room, or check out the pool schedule to plan your water-based recreation.

Bennington Tennis Center, Bennington, Vermont

The Bennington Tennis Center (BTC) is a locally owned full-service indoor and outdoor tennis club located off Northside Drive in Bennington. In addition to four climate-controlled tennis courts for year-round play, BTC offers professional private and group lessons for adults and kids of all skill levels. BTC also maintains a full-service pro shop offering racquet sales and service. 

BTC is part of Bennington Aces, which is dedicated to providing underserved youth in the community with tennis and academic opportunities through partnerships with local schools.  

A young girl getting ready for a game of tennis. Photo credit: Bennington Tennis Center
A young girl getting ready for a game of tennis. Photo credit: Bennington Tennis Center

After a day of recreating in and around Bennington, head into town for a scrumptious meal. Need ideas? Check out all of the awesome eateries in Bennington.