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Fun Things to Do in Berkshire Winter

Posted on February 25, 2024Written by Nancy Macy c/o 1Berkshire
Updated on February 26, 2024

A young black man peers through a light installation at The Mount as part of an event called NightWood.

Your guide to some of the best things to do outdoors in the Berkshires during winter, and the coziest ways to warm up. 

The Berkshires is stunning in all four seasons, but there’s nothing quite like crisp winter air and a fresh snowfall to make it magical. Whether you enjoy outdoor sports, an evening walk through shimmering holiday lights, or sipping something tasty beside a fireplace, here is a short list of wonderful winter experiences in the Berkshires.

Holiday Light Celebrations

Imagine yourself on a clear winter night walking through artful light and sound installations in the gardens and woodlands surrounding historic Naumkeag, The Mount, and Hancock Shaker Village. If you’re picturing a winter wonderland, you’ve got it right. These events often sell out, so purchase your tickets early. Winterlights at Naumkeag estate is one of the largest displays of its kind. Your ticket includes the shuttle ride from downtown parking in picturesque Stockbridge. Radiant Nights at Hancock Shaker Village, complete with farm animals and activities for kids, is a great choice for families. NightWood at The Mount is an immersive multisensory experience staged along a ¾-mile walking trail on the grounds of Edith Wharton’s Gilded Age estate in Lenox. 

Warm Fires, Hot Meals

After a winter-weather outdoor adventure, what’s better than settling in beside a fireplace with a cold brew, hot chocolate, or belly-warming bite to eat? Head for local favorites Freight Yard Pub & Restaurant, Brava, and The Lion’s Den, where you’ll also find live music on weekends. For dinner with a fiery flare and a menu featuring Berkshire grown and sourced ingredients, Casita Restaurant & Bar at MASS MoCA is good bet.

Shop for Outdoor Gear, and More

Winter outdoor activities are weather-permitting in the Berkshires. If you’re looking for an alternative to spending the day outside, there are plenty of unique stores filled with books, antiques, clothing, and handmade gifts. Or fine art galleries such as ROAM. And why not stop in at Nature’s Closet and Arcadian Shop for all the cold-weather gear and outerwear you need for your next outing?

Wine (and Donut) Tastings

The well-stocked shelves at Dare Bottleshop & Provisions offer plenty of options for warming up a winter evening after a day outdoors. Their Holiday Tasting Series is the perfect opportunity for discovering new wines or finding the ideal bottle for your next dinner party. And, while donuts may not be the usual pairing with your favorite malbec, the made-to-order variety from Shire Donuts is an experience you don’t want to miss, so Dare is hosting Holiday Pop-Ups this year where you can taste these decadent delights for yourself.

Discover more ways to explore the Berkshires in winter. We’ve got fun ideas for everyone!

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