Your Ultimate Winter Play Guide: 13 Fun and Beautiful Winter Trips to Plan Now

8. Explore the Best of the Backcountry

The Catamount Trail stretches for 300 miles through some of Vermont’s most spectacular terrain—a wild tableau of snowy peaks, chutes, and forest. Amid that territory, one section near Bolton Valley Ski Area, 25 miles east of Burlington, stands out, offering access to some of the best backcountry skiing in New England.

Trail options are almost limitless here, but consider tackling the nine-mile tour linking Bolton Valley with Stowe’s Trapp Family Lodge (founded by the family of The Sound of Music fame), leading through hardwood forests perfectly spaced for tree skiing. When you finally arrive at the lodge, a brat platter with housemade pickles and an Austrian beer await. Bolton Valley offers guides and shuttles as well as backcountry clinics (from $175).

Next door in New Hampshire, the Appalachian Mountain Club’s High Cabin sits at 2,700 feet in Mount Cardigan State Park and serves as a perfect base for a few days of playing around in the snow. The 1938 cabin has one room with six beds (sleeping up to 12 people total), a propane stove, and a woodstove for keeping warm ($169 a night per person). From there you can tour about half a mile to the exposed summit of 3,121-foot Mount Cardigan, or work your way over to Duke’s Ski Trail off Firescrew Mountain—one of Mount Cardigan’s three summits—for a run that will drop you close to the Cardigan Lodge, a full-service hut where a hot family-style meal comes with your overnight stay (from $177).

9. Learn Something New, Like, Yep, Snowkiting

Kiteboarding on snow may sound daunting, but it’s easier to learn than on water. For starters, you use skis, you’re already standing up, and a gentle breeze will suffice. Book a lesson with Kite Riders in Fitchburg, Wisconsin, on the southern outskirts of Madison.

Or head 230 miles west to Clear Lake, Iowa; on February 18, it hosts the largest kite festival in the Midwest, where you can also book a snowkiting lesson.

Want to try your hand at fat biking on snow? Lake Tahoe’s Northstar resort is home to 20 miles of fat-biking and cross-country trails. Rent a rig from the Northstar Cross Country Center and set out solo, or with a guide, on one of eight beginner-friendly routes.

East Coasters can book a guide with Water Bikes of Buffalo, in that New York city’s Canalside neighborhood—the only place in the world where you can learn to ice-bike. Picture a bicycle atop a sled with broad, stable runners and a fork with skate-like blades that allow you to turn.