Best Places to Snowshoe in the Berkshires

Woman in a blue and white ski coat with ski poles cross country skiing.

Photo: Courtesy of Hilltop Orchards

It’s time to break out the winter gear and start exploring new destinations to challenge your inner Olympian. You could wax your skis or sharpen your ice skates. But, if you’re looking for something new to try this year, the answer is simple. Snowshoeing. And if you’re looking for the best places to snowshoe in the Berkshires, you’re in luck. Because, the rolling hills of western Massachusetts are a mecca for winter sports lovers. And the Staveleigh House Bed and Breakfast is in the heart of it all.

The beauty of snowshoeing is that, other than the snowshoes themselves and maybe some hiking poles, all you need is some warm clothing. And, you can move at your own pace, so it’s perfect for beginners. It’s best to dress in layers, however, as once you build up a sweat, you’ll be shedding layers like crazy.

When choosing a destination for your outdoor snowshoeing adventure, definitely think about the terrain and the scenery. The Berkshires offers an abundance of both.

If you want challenging vertical climbs, we’ve got that. Looking for a leisurely trek through a pine forest? Got that too. So, let’s break down the best places to snowshoe near us in the Berkshires.

  • Beartown State Forest, Monterey, MA The 1.5-mile Benedict Pond trail is an easy introduction to this winter wonderland. Though you may be sharing the route with cross-country skiers and winter hikers, 8 additional trails offer more challenging terrain and magnificent vistas.
  • Hilltop Orchards, Richmond, MA The ideal spot for a guided full moon trek, followed by a bonfire, Hilltop Orchards has the added benefit of an onsite winery for apres skiing fun. Trails range from easy to moderate, but all offer gorgeous scenery. Great place for a picnic too!
  • Kennedy Park, Lenox, MA This town-owned property offers 15 miles of groomed trails create by old carriage roads. Pick up a map at the Arcadian shop before heading out for your morning or afternoon adventure.
  • October Mountain State Forest, Lee, MA October Mountain State Forest is the largest in the state of Massachusetts. Hence the diversity of terrain offered here. Trails here range from easy to moderate, with lengths of less than 2 miles to well over 17 miles.
  • Pleasant Valley Wildlife Sanctuary, Lenox, MA The trails of the Pleasant Valley Wildlife Sanctuary traverse meadows, wetlands, and forests. Along the way, you may spot birds and beavers active in their natural habitats. Encompassing a total of 1,142 acres, this Audubon property provides a great introduction to the sport.
  • Lime Kiln Farm, Sheffield, MA Two mile of scenic trails through rolling hayfields and pine forest lead to a magnificent view of Mount Everett.

After an exhilarating day exploring the countryside on snowshoes, you’ll need a little TLC back at the Inn. Stake out a place in front of the fireplace, or retreat to your cozy room for a well-earned nap. In the morning, we’ll treat you to our gourmet breakfast, then send you on your way to another adventure in the great outdoors of the Berkshires.