Winter in the Berkshires brings snow-covered mountains, peaceful woodland trails, and plenty of reasons to bundle up and explore. Spend your days skiing down the slopes, snowshoeing through the forest, or taking a scenic drive through the countryside.
After a day outside, come back to Devonfield and settle in beside the living room fire. Enjoy something sweet from our late-night dessert bar and leave the day’s adventures behind. We’d love to welcome you to Devonfield for a cozy winter getaway.
Why Visit The Berkshires In Winter?
One of the pleasures of winter in the Berkshires is having time to linger between outings. Spend the morning exploring snowy trails, then browse the shops in Lenox or stop for lunch in Stockbridge.
You can fill your days with outdoor adventures or take the scenic route back to Lee. With charming towns, beautiful countryside, and plenty to do indoors, there’s no need to plan every hour.
Go Skiing In The Berkshires
Four ski mountains within driving distance of Devonfield give you plenty of choices, from first lessons to challenging runs. Each has its own appeal.
Ski Butternut In Great Barrington
Been a while since you’ve strapped on skis? Ski Butternut offers beginner packages with lessons, equipment rentals, and lift access to help you get back into the swing of things. Gentle terrain makes it a welcoming place to learn, and snow tubing offers a change of pace.
Jiminy Peak In Hancock
Who says the fun has to end when the sun goes down? Jiminy Peak has 45 trails, ranging from easy runs to challenging double black diamonds. Three terrain parks offer more excitement, and night skiing lets you squeeze in a few extra runs under the lights.
Catamount Mountain Resort In South Egremont
At Catamount, you can ski across the Massachusetts and New York state line without leaving the mountain. Their 44 trails include gentle beginner runs and Catapult, one of the steepest trails in the Berkshires. Prefer something gentler? Follow Ridge Run into Promenade for a long, easier descent.
Bousquet Mountain In Pittsfield
There’s a little Berkshire history beneath your skis at Bousquet Mountain. Established in 1932, it introduced America’s first night skiing in 1936. Today, you can explore 23 trails, try the terrain park, or swap your skis for a snow tube.
Check each mountain’s snow report, lift hours, and lesson availability before heading out.
Explore Snowshoeing And Cross-Country Skiing In The Berkshires
Snowshoeing and cross-country skiing let you enjoy the woods without the bustle of a ski mountain. Follow old carriage roads, take in snowy forest views, and stop whenever something catches your eye.
At Notchview in Windsor, more than 25 miles of trails cross spruce forests and open fields. Groomed routes welcome cross-country skiers, while snowshoers can travel beside the ski trails or explore the backcountry. Need equipment? The Budd Visitor Center rents skis and snowshoes during the season. Pick up a trail map there before setting off.
Closer to Devonfield, Kennedy Park in Lenox offers nearly 15 miles of wooded trails and old carriage roads. The Arcadian Shop sits right at a park trailhead and rents snowshoes in winter. Pick up a pair and head into the woods, or bring your own cross-country skis.
Local tip: Check trail conditions and rental availability before you set out. A good snowfall makes all the difference.
What Else Can You Do In The Berkshires In Winter?
Winter activities in the Berkshires go well beyond the ski trails. Leave room for sightseeing, shopping, and a few local favorites, especially when the weather changes your plans.
- Take a scenic winter drive. Travel between Lee, Lenox, and Stockbridge for snowy hills, historic homes, and small-town scenery. Stop for coffee when something catches your eye.
- Spend an afternoon at a museum. See the famous illustrations at the Norman Rockwell Museum in Stockbridge. You’ll find more Berkshires museums and historic sites to explore when you’re ready to warm up indoors.
- Go ice skating. Pittsfield’s seasonal outdoor rink at Wahconah Park offers skating when conditions allow. Bring your own skates and check the city’s opening updates before you go.
- Browse the local shops. Wander downtown Lee’s boutiques and specialty stores, then look for a bargain or two at the Lee Premium Outlets.
- Enjoy a little holiday magic. During the holiday season, Naumkeag’s Winterlights fills its Stockbridge gardens with sparkling displays. Make time for other holiday traditions in the Berkshires, too.
You can easily work these stops into a weekend of winter adventures or make a full day of exploring. Our Berkshires trip-planning guide has even more ideas to help you plan your visit.
Plan Your Cozy Berkshires Winter Getaway
Coming back to a warm inn after a day outside is one of winter’s small pleasures. Settle beside Devonfield’s living room fireplace, or find a late-night treat at our dessert bar. Our guest pantry is also open around the clock for snacks and drinks.
The Roosevelt Suite and Queen’s Cottage both have wood-burning fireplaces and spa tubs for cozy evenings in. Come morning, enjoy our country breakfast before heading out again.
Browse our rooms and suites and make this winter in the Berkshires one to remember.
Photo Credit: © JMichl from Getty Images Signature via canva.com, © Creativaimage from Getty Images Signature via canva.com
