Best of Winter in the Berkshires

With a fresh layer of snow, the best of winter in the Berkshires is happening now. The snow-covered mountains sparkle in the sunlight, and brilliant stars light up the night sky. It’s a picture-perfect time to visit western Massachusetts. Cozy before a warm fire at our elegant country retreat, or enjoy wild outdoor fun in our winter wonderland.

Play Outdoors

1. Downhill Skiing and Snowboarding

Finding your groove on the slopes is easy with five top-notch ski resorts in the neighborhood. Travel north to Jiminy Peak or Bousquet Mountain for an exhilarating day carving down a challenging black diamond run. Or meander to Ski Butternut, Berkshire East, or Catamount Mountain to mix it up in a terrain park.

2. Cross-Country Skiing and Snowshoeing

Nothing gets the heart pumping like cross-country skiing or snowshoeing through the woods. At the Canterbury Farm Ski Touring Center, you can traverse 22 kilometers of groomed trails through dense forest with a summit view of Mount Greylock. Bring your equipment or rent on-site.

3. Sledding and Tubing

Relive your youthful enthusiasm for sledding or tubing down a steep hill with the wind in your hair and a smile on your face. It’s a rush for sure on that downhill ride. But if you prefer to skip the long uphill trek pulling your sled behind, head to Bousquet Mountain and let their Carpet Lift whisk you to the top. A 450-foot run down any of 8 lanes will take your breath away.

4. Take a Winter Hike

Winter hiking in the Berkshires offers a chance to experience the region’s beauty in a more peaceful and less crowded setting.

Popular spots include Mount Greylock, the highest peak in Massachusetts, where winter hiking offers breathtaking views.
- Remember that some trails may require traction devices like crampons, especially after a snowstorm.

Monument Mountain in Great Barrington is another popular trail. It offers a moderate hike and a panoramic view of the Berkshires.

Whether you prefer a short jaunt or a more strenuous trek, the winter landscape will make every step worthwhile.

Stay Inside

1. Museum Hopping

World-class museums pepper the hills of western Massachusetts. From European masterpieces to iconic American illustrations, the quality and quantity of art galleries and museums in the Berkshires are second to none. Spend the day wandering the art world at these magnificent art centers.

Sterling and Francine Clark Art Institute
Williams College Museum of Art
Mass MoCA
Berkshire Museum
Norman Rockwell Museum
Schantz Galleries

2. Wine Tasting and Touring

Dashing through the snow is fine, but sipping and swirling a vintage glass of wine can be as fun. Perhaps you didn’t know that the Berkshires is home to five quality wineries. Each location produces an excellent variety of award-winning wines. Designate a driver and explore the Berkshires’ main streets and back roads to search for an exceptional bottle of wine to decant back in your room at the Inn.

3. Craft Breweries

Similarly, craft brewers abound in the Berkshires. Each of the six breweries within a 15- to 45-minute drive of our Inn offers a unique beer style. Some even produce hard cider, a different take on brewing. Plan your route accordingly to sample the best of the Berkshire brews.

4. Dine Around Town

The Berkshire region offers a range of dining experiences near Lee, Lenox, and Stockbridge.

For casual fare, The Red Lion Inn in Stockbridge serves hearty comfort food with a historic flair.
Bistro Zinc in Lenox is a culinary staple offering a cozy French vibe.
In Lee, Café Triskele also offers a charming French-inspired menu and warm atmosphere, perfect for a relaxed yet refined meal.

These spots offer a taste of the Berkshires’ rich culinary diversity.

Winter Getaway to the Berkshires

Baby, it’s cold outside, but that won’t deter you from having a blast on a winter getaway to the Berkshires. Whether you play inside or out, the best winter in the Berkshires awaits you at Devonfield Inn. Pack up your snow toys and woolies for a trip to western Massachusetts this season. Book your getaway. Our winter wonderland is just what the doctor ordered.