Snowshoeing & Cross-Country Skiing in the Berkshires: A Winter Wonderland

Winter in the Berkshires transforms the landscape into a serene playground for snowshoeing and cross-country skiing enthusiasts. Whether you’re a seasoned skier or a beginner eager to explore the snowy trails, the Berkshires offer a variety of destinations to suit every skill level. Here’s a guide to some of the best spots to enjoy these winter sports.

Top Cross-Country Skiing & Snowshoeing Destinations in the Berkshires

  • Notchview Reservation – Windsor, MA: Managed by The Trustees, Notchview spans over 3,200 acres of forest and meadows in the Hoosac Range. It offers 17 km of groomed trails for classic skiing and 12 km for skate skiing. Snowshoers can explore designated trails or venture alongside the ski tracks. The Budd Visitor Center provides equipment rentals, a café, and warm seating areas.
  • Canterbury Farm – Becket, MA: Nestled at 1,650 feet elevation, Canterbury Farm boasts 22 km of groomed trails suitable for all levels. The farm offers rentals for skis, snowshoes, and ice skates, along with certified lessons. After a day on the trails, relax in the historic lodge with a hot drink by the fire.
  • Maple Corner Farm – Granville, MA: This family-run farm provides 20 km of groomed ski trails and 10 km of snowshoe paths. The trails wind through pastures, forests, and maple groves, offering a picturesque setting for winter sports. Equipment rentals and a cozy lodge with a snack bar enhance the experience.
  • Hilltop Orchards – Richmond, MA: Set on a 200-acre property, Hilltop Orchards offers 4 miles of groomed trails designed by Olympic skier John Morton. The trails meander through orchards and woods, providing scenic views of the Berkshire Mountains. The orchard also hosts guided full moon snowshoe walks with bonfires.
  • Kennedy Park – Lenox, MA: A town-owned hardwood forest with nearly 15 miles of groomed trails, Kennedy Park is ideal for snowshoers seeking easy to moderate terrain. The Arcadia Shop in Lenox offers snowshoe rentals for those looking to explore the park’s scenic paths.
  • Mount Greylock State Reservation – Lanesborough, MA: As the highest point in Massachusetts, Mount Greylock offers challenging terrain for experienced snowshoers. The summit provides breathtaking views of the surrounding landscape, making the effort worthwhile for those seeking a more strenuous adventure.

Tips for Enjoying Winter Sports in the Berkshires

  • Dress in Layers: Wear moisture-wicking base layers, insulating mid-layers, and waterproof outer layers to stay warm and dry.​

  • Check Trail Conditions: Always verify trail status and conditions before heading out, as weather can affect accessibility.​

  • Stay Hydrated and Energized: Bring water and snacks to maintain energy levels during your adventure.​

  • Respect Nature: Stay on designated trails to protect the environment and ensure safety.​

Embrace the winter season by exploring the snowy trails of the Berkshires. Whether you’re gliding through groomed tracks or trekking through untouched snow, the region offers a perfect setting for winter sports enthusiasts.