10 Winter Activities Around Stockbridge, MA

Are you and your family headed to Stockbridge, MA this winter? The quintessential New England town still has plenty to offer during the winter months and is incredibly picturesque. (There’s a reason Norman Rockwell painted so many snow scenes in the region!). 

Here are some of our favorite winter activities that are fun for the entire family in Stockbridge, MA.

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1. The Stockbridge Library

Do you love all things history? Is your child working on a school project? The Stockbridge Library and museum are loaded with fantastic resources about local history and more. The library offers a terrific selection of virtual programming as well.

2. Norman Rockwell Museum

The Norman Rockwell Museum is home to the world's largest collection of original Norman Rockwell art, many pieces were inspired by Stockbridge and the Berkshires!

3. Skiing

There’s plenty of skiing near Stockbridge, MA. Whether it’s your first time hitting the slopes or you’re a pro, you can find an outdoor recreation area that is perfect for your skill level. 

4. Hollywood in the Berkshires

Berkshire County is a hub for animation and special effects, and local residents have been integral to the production of big-budget movies and TV shows for the past several decades. All this local influence is on display at AniMagic, which is free and open by appointment only!

5. Bousquet

If you and your family are interested in other outdoor winter sports beyond skiing, check out this multi-purpose ski resort that offers an adventure park, camps, a ropes course & more.

6. Hilltop Orchards

This orchard is known as a natural oasis offering wine tastings and full moon hikes, but in winter the hiking trails turn into cross-country ski tracks. Hilltop Orchards rents out skis and snowshoes and offers PSIA-certified instruction for those just starting out. There’s even an option for a special guided full moon snowshoe trek and bonfire!

7. Massachusetts Museum of Contemporary Art

Ready to escape the cold and be inspired by some of the latest and greatest contemporary art? MASS MoCA is the place to be and offers a variety of seasonal art installations that are sure to catch your eye.

8. Ice Fishing on Stockbridge Bowl

A popular boating spot in the summer months, The Stockbridge Bowl, a 372-acre pond, offers ice fishing for the whole family as it gets chillier outside. Trek outside and do your best to try and catch one of the 13 species of fish that reside here!

9. Herman Melville’s Arrowhead

For over forty years, the Historical Society has worked hard to preserve Herman Melville’s Arrowhead. You and your family will love learning about the history of the homestead and some of the special events hosted there.

10. Berkshire Museum

The Berkshire Museum combines art, science, and history to create thought-provoking experiences for visitors of all ages. No matter how old you are, the collection of more than 40,000 is sure to pique your interest and teach you something new about the Berkshires in a novel way.

Plan Your Stockbridge, MA Winter Stay

Ready to plan your winter getaway to the Berkshires and make new memories with your family? Consider staying at The Red Lion Inn!


Contact Us Today!

Book your stay for your trip to Stockbridge today by calling us at (413) 298-5545. We’re looking forward to greeting you and your family upon arrival and giving you more recommendations on seasonal and regional attractions that are open this winter!