Hit the Trail with the Berkshires’ Best Cross Country Skiing and Snowshoeing

It’s been my experience that there are two ways to get through a winter in the Berkshires. You can stay cooped up indoors and pray for spring. Or you can get out there and take advantage of all of the winter sports activities that blow in with the first snow. I can tell you firsthand that the cold months go by a lot faster when you do the latter. And there’s no better way to spend some time in the frosty outdoors than with a few hours of cross-country skiing and snowshoeing. After all, the “Nordic” sports provide great exercise while allowing you the time to casually glide along trails that showcase a natural, snow-covered setting right out of a Currier & Ives painting. Just to help get you started, here are a few of the best, and most popular, cross-country skiing and snowshoeing destinations in and around the Berkshires.


Notchview is located in Windsor, MA. Its 3,000 acres of rolling terrain and 25 miles of trails offer an idyllic escape for cross-country skiers and snowshoeing alike. Seventeen kilometers of trails are groomed and track- set for classic cross-country skiing. You can also go off track and explore the backcountry, or snowshoe alongside the ski trails. Much of the reservation is above 2,000 feet – which means snow for more than 80 days each year. Rentals are available. Visitor center and café on premise.

Hilltop Orchards

Hilltop Orchards best known for apples and the Furnace Brook Winery, is popular among both locals and visitors. Nestled in the nearby rolling hills of Richmond, MA., Hilltop offers miles of groomed moderate and challenging terrain with separate trails specifically designed for snowshoeing. Don’t miss out on the Guided Full Moon Snowshoe Trek & Bonfire. Lessons and equipment rentals are available on premise. The farm store and winery are also open daily.

Kennedy Park

Kennedy Park is situated on the outskirts of the historic village of Lenox. The Park’s 502 acres of tree lined forest features 15 miles of trails carved out of a network of old carriage roads. While there are a variety of terrains, including several moderate climbs, the park’s trails are predominately flat and smooth – perfect for both cross-country skiing and snowshoeing. However, the trails are not groomed. Rentals available at the nearby Arcadian Shop, which is located at one of the park’s trailheads.

Pittsfield State Forest

Pittsfield State Forest is a sprawling 1000-acre forest located in the town of Pittsfield. Open year-round, it offers 30 miles of trails – many specifically marked for winter activity. It’s a pretty rustic set-up. No bells and whistles here. Just lots of majestic outdoor scenery and hearty trail excursions. There is a ski lodge available for use in the winter. For rentals, try out Plaine’s Bike Ski and Snowboard in Pittsfield.

Mt. Greylock

Mt. Greylock Is the ultimate challenge for snowshoeing in Western Massachusetts. Reaching a peak of 3,491 feet, it is the highest point in Southern New England. What’s more, there are few mountains in the Northeast with as much diversity and access. There are over 70 miles of trails, many of which can be trekked in winter. Most of these climbs are steep and catch-your-breath challenging, definitely not for the inexperienced. But if you do reach the top, take a break, sip something warm and bask in a 60 – 90 mile view of five states. The best rental option is Berkshire Outfitters in nearby Adams.

There’s nothing quite like winter sports here in the Berkshires. And now that you’re in the know on where to go, grab those snowshoes and XC skis and get out there and explore all that our magnificent snow covered forests have to offer. Hey. The next thing you know it’ll be spring.