The Berkshires Blog

Outdoor Adventure Deals: Winter in the Berkshires

By Nancy Macy

Get away to the Berkshires, where stunning natural landscapes set the stage for exciting outdoor adventure. Play by day on our beautiful lakes and mountain trails, then explore our vibrant cultural and farm-to-table culinary scene. Whatever your idea of a relaxing escape, you’ll find it here, along with a warm welcome for all.

Discover more of what the Berkshires have to offer for outdoor fun from these local businesses. In addition to incredible downhill and cross-country skiing venues, the Berkshires offers among the best resources in the region for outdoor gear, equipment rentals and information on nearby places to use it. They are among the best resources in the region for outdoor gear, equipment rentals and information on nearby places to use it. You’ll even find current snow and ski conditions so you can get the most out of your trip.

Let the games begin. Get outdoors this winter.

Location: Canyon Ranch


For equipment and outdoor gear, visit the Arcadian Shop in Lenox. As the premier adventure outfitter in the Berkshires, they carry a wide inventory of ski and snow gear for men, women, and kids. Rent or demo equipment, lace up a new pair of boots, try on the latest in outdoor performance wear, or pick up some warm socks and a cozy hat. They even have gear and toys for dogs to keep your canine companion happy too. Plus, they carry GoPro cameras and accessories for capturing those adrenaline-filled moments out on the trail. Don’t feel comfortable going out alone? They can help with their guide services.

From the parking lot at the Arcadian Shop, you’ll find easy access to the miles of trails in scenic Kennedy Park. This vast eco-system, bordered by conservation land on one end and downtown Lenox on the other, is the ideal spot to start playing with your new gear.

If you’re looking for big mountain fun, head for Jiminy Peak Mountain Resort in Hancock. Offering a four-season adventure park this is the largest ski and snowboard resort in southern New England, with more than 45 trails, nine lifts, lodging, dining, and a ski shop right on the mountain. The resort’s Mountain Coaster offers a thrilling ride in all seasons and a network of groomed snowshoe trails provides a tranquil way to enjoy the Berkshires outdoors. Be sure to make your reservations and stay right on the mountain.

Take a walk on the wild side.

For information about other snowshoe and cross-country skiing trails in the area, contact the Western Massachusetts Cross Country Ski Area Association. They always have up to date trail info and this group of seven ski areas offers diverse terrain and scenic views of the surrounding Berkshire hills. You’ll find miles of groomed trails, rentals, and lessons plus lodging at most locations. Experience the incredible peace of gliding over snow-covered trails carved through meadows, orchards and state forests with a wide-open, deep blue Berkshire sky overhead. There’s truly nothing like it on a clear winter’s day!

Are you looking for opportunities to combine your love of the outdoors with a bit of culture and history? The Upper Housatonic Valley Heritage Area (Housatonic Heritage) works in partnership with the National Park Service and local conservation and preservation organizations to provide access to the area’s rich natural and historical resources. Housatonic Heritage organizes events throughout the region, including guided walks in the Berkshires and nearby Litchfield County, Connecticut. No matter the time of year be sure to check out their Arts Heritage Trail and in the fall reserve a spot on one of their Heritage Walks, all of which are free. Each is another way to experience the unique beauty of the Berkshires.

Located less than a three-hour drive from both New York City and Boston, the Berkshires are a world away from the busy pace of city life. Special deals and packages make planning a vacation here easy and affordable. Pack a bag and head for these hills. You’re going to love it in the Berkshires!

Nancy Macy is a freelance writer and editor based in the Berkshires.