Fun Winter Getaways

From snow-covered mountains to frozen lakes, discover the beauty of winter with an adventure in the great outdoors! 

If the arrival of cold weather has you thinking about fun ways to play outside, it’s time to book your winter escape in the Berkshires. Our short-list of ideas for winter activities—plus cozy cabins and resort lodging—puts you in the heart of it all! 

Book a Ski & Stay Package

In the Berkshires, a winter escape can mean staying at roadside motels, chain hotels, or a luxury resort. When you book any lodging near a Berkshire ski area, even if it’s not on the mountain, be sure to ask if discounts on ski passes, equipment rentals, or lessons are available for guests. 

Ski Butternut.

Go Skiing or Tubing, at Night

If you love spending time in nature, there is nothing quite as magical as hitting the trails under a moonlit sky. In the winter months, that means cross-country ski touring at Notchview or Maple Corner Farm and downhill skiing after dark at Bousquet, Catamount, and Jiminy Peak Mountain Resort. On weekend evenings, you can also go tubing at Ski Butternut or Berkshire East (reserve ahead to guarantee your desired time slot).

Head for the Backcountry

State forests and portions of the Appalachian Trail offer backcountry opportunities for experienced (and well-prepared) skiers, snowmobilers, and winter hikers. There are well-maintained trails at Greylock Glen, Pittsfield State Forest, and Beartown’s winter recreation area. Mount Greylock is famous for its Thunderbolt Trail. Be sure to visit local outfitters for winter-appropriate gear and tips on finding trails best suited to your activity and ability.

Huttopia Berkshires.

Stay in a Cabin

Love the idea of spending the night in a cabin in the mountains, just steps away from great skiing? You’ll find the best of both worlds at Huttopia Berkshires. The resort’s mix of lodging options includes 11 year-round cabins (with toasty-warm woodstoves) overlooking Jiminy Peak. If you’re heading to Catamount, book a stay in the Scandinavian-style cabins at Prospect Berkshires.  The dreamy lakeside setting is peaceful, the elevated menu highlights seasonal local ingredients, and there’s a sauna to take off winter’s chill.

Go Ice Fishing

When you start seeing huts appear on frozen lakes and ponds, it’s time to head to Onota Boat Livery for ice-fishing supplies. This family-run marina and shop sits next to one of the largest and most scenic lakes in the central Berkshires. Other popular spots for winter anglers are Pontoosuc Lake, Stockbridge Bowl, and Benedict Pond.

Aprés-Everything

Whether your idea of relaxing after an adventure is a soothing spa treatment or a pub night with live music or big-screen TVs, you’ll find it in the Berkshires. Enjoy a massage at Miraval Berkshires or Canyon Ranch. Head to the Lion’s Den or Freight Yard Pub for local bands, light fare, and microbrews. Or sip craft cocktails by the fireplace at an historic inn. 

Even in a mild winter, there’s plenty to see and do in the Berkshires. If you’re all about getting outdoors, be sure to check conditions ahead of your visit. No matter what brings you here in the winter months, we look forward to giving you a warm welcome!

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