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Even in the best of times, winter can be a long and unforgiving season. Shorter days and wind chill can make you feel like hibernating ’til it’s over, but it doesn’t have to be unbearable. In fact, our insiders have found some pretty sweet ways in and around Charlottesville to beat cabin fever and make the most of the season.

Easy Hike Around Woolen Mills:

Don’t let the cold keep you indoors this winter. Bundle up the whole family for a walk through wooded trails along Moore’s Creek and check out the new pedestrian bridge. When it’s time to warm up, head to The Wool Factory for some coffee or hot cocoa from The Workshop or make a reservation for outdoor dining and brews at Selvedge Brewery

The Saunders-Monticello Trail

The crushed gravel trail that winds gently up the mountain to Monticello is a walk suitable for all ages. Dogs are welcome on the lower portion of the trail, but once the wooden walkways begin, it’s humans only. If you make it all the way to the top, reward yourself with a cozy cup of hot cocoa at the Monticello Visitor’s Center. Nature, history and a sweet treat. What could be better?

The Trails at James Madison’s Montpelier:

Less than 30 minutes outside Charlottesville, Montpelier boasts eight miles of hiking and walking trails. Walk along The Landmark Forest and Demonstration Forest trails to see rare old growth and transitional forests with oak, beech and tulip tree canopies. Other trails on the property include the Montpelier-Grelen Trail and the Montpelier Civil War trail. Dogs on-leash are welcome.

Highland Trails:

Your presidential trail tour can keep on going at James Monroe Highland, the home of the fifth president. Just up the road from Monticello, you’ll find six Highland Trails plus the mountain access road ranging in length from .2 up to 2.1 miles. String a few together for a longer hike. Dogs are not allowed on the trails except on designated days.

Wintergreen Resort:

Just 45 minutes from Charlottesville in Nelson County, Wintergreen Resort is an outdoor wonderland, and never more so than during the winter months. If zipping down slopes on skis or a snowboard aren’t your thing, check out The Plunge tubing park and the miles of hiking trails with breathtaking overlooks. Check the website for lift ticket specials like the Mission: Four’dable, which gets you four lift tickets to use anytime during the 2020-21 season for $249. Available through Dec. 18

Indian Summer Guide Service

The Central Virginia countryside is gorgeous year-round, and you’ll enjoy it even more on horseback! No riding experience? That’s no problem with Indian Summer Guide Service. You and a group can take a guided ride through area vineyards, into the mountains and across meadows and streams. Riders must be 12 or older, 250 lbs or less, and able to mount and dismount with only a mounting block for assistance.


Charlottesville’s only locally owned spin-hub has regular classes and now offers an at-home bike rental program. The bonus? Classes taught by Charlottesville Insider Ian Dillard


The instructions for this barre studio are simple: Show up. Be you. Leave stronger. And with online classes available, you don’t have to leave home to get stronger!