22 Fun & Festive Things to Do this Winter in the Berkshires

A man wearing snowshoes

This article has links to products and services we love, which we may make commission from.

If you’re looking for a winter getaway that will keep you entertained from morning to night, look no further than the Berkshires in Massachusetts. 

This charming corner of New England has plenty of activities to keep you busy, whether you’re into skiing and snowboarding, checking out museums and art galleries, or simply taking in the beautiful winter views.

To help plan your visit, we compiled fun activities, destinations, and festive events you can enjoy during winter in the Berkshires.

And if you’re wondering where to stay in the Berkshires in winter as the base of all your adventures, check this guide.

Things to Do in the Berkshires in the Winter

Enjoy the Bay State Winter Games

If you love winter sports, the annual Bay State Winter Games is the event for you.

Figure skating, ice skating, curling, and futsal are the featured games, making this event a thrill for anyone who loves these competitions.

Set in the Berkshires, you can explore the area when you’re not cheering on your favorite teams.

The Bay State Winter Games are some of the best Berkshires winter activities every year.

Ski Berkshire East

For a downhill skiing experience that is a little off the beaten path, make the trip to Berkshire East Mountain Resort (66 Thunder Mountain Rd, Charlemont).

The resort is commonly described as a hidden gem, and it has the same atmosphere as the most iconic small-town New England ski resorts.

Berkshire East even features as one of our top places to ski in New England.

High-quality snowmaking and trail grooming, as well as rentals, lessons, and even on-site dining make this a great afternoon to spend with the whole family.

They are also the first ski area to produce 100% of its electricity from off-site renewable energy.

Berkshire East is one of the best Berkshires winter getaways in the region.

Looking to explore more activities and destinations in New England? Check this guide.

Hike the Snowshoe Cascades Trail in North Adams

For a simple, stunning winter snowshoe adventure, visit the Cascade Trail in North Adams (22 Brickyard Ct, North Adams).

Specifically maintained by the Trustees of Reservations of Western Massachusetts for cross-country skiing and snowshoeing in the winter, this trail has all the natural wonders you’re looking for.

The shining star of this trail is the cascading waterfall, but the forest is gorgeous for the entire hour-and-a-half hike.

North Adams also features in our guide to Massachusetts in fall.

A man wearing snowshoes


If you’d like to spend some of your time indoors in the Berkshires in winter, then a museum visit is a must.

MASS MoCA (1040 MASS MoCA Way, North Adams) is among the largest contemporary art museums in the world- with 250,000 square feet of open and naturally lit space.

The museum features art exhibits by both well-known and emerging artists, dance performances, films with live music, documentaries, educational programs, and more.

Over the winter season, the museum hosts a variety of live music, performance art, and theater events- check their calendar for an updated schedule.

This is also one of our favorite winter activities in MA to escape the cold for a bit.

The MASS MoCA sign in North Adams Massachusetts

Visit The Clark Art Institute

Clark Art Institute (225 South St, Williamstown) is a museum and research center featuring a wide collection of American and European paintings, photography, and sculpture.

It also features outdoor exhibits.

Special exhibits and events are hosted during the winter season so make sure to check out the museum’s calendar for updates.

The Clark is one of our favorite date spots in the Berkshires, too!

The Clark Art Institute entrance sign in Williamstown Massachusetts

Experience Project Snowshoe

Once you’ve finished admiring all the art at the Clark Art Institute, head out into the snow and walk through the sprawling grounds.

While this place is one of the most respected art museums in the world, what makes it even more special in the winter is the option for a free snowshoeing adventure!

Project Snowshoe offers complimentary snowshoes to any patron that wants to explore the 140 acres of natural land around the institute.

Visit Jiminy Peak Mountain Resort

Get the most out of your Berkshires skiing experience at the Jiminy Peak Mountain Resort (37 Corey Rd, Hancock), a leader in the New England skiing and snowboarding world.

Skiing in the Berkshires is always a fun thing to do in Massachusetts in winter, and Jiminy is one of the best resorts out there.

Boasting more than 45 trails over 167 acres, you could spend a whole day on the slopes.

The resort also sources 100% of its electrical energy from renewable resources.

Jiminy Peak is one of our favorite spots for skiing in Massachusetts, so don’t miss out!

Visit a Shaker Village for Hancock Holiday Nights

Travel back to Christmastime at the Hancock Shaker Village (1843 W Housatonic St, Hancock) for Hancock Holiday Nights, a festive celebration of the holiday season.

Stroll through the 19th-century Shaker village, which has been adorned with decorations and lit up with artful holiday lights.

With lots of special events, warm holiday cocktails, and a roaring fire to enjoy, you’ll love taking your whole family to this wintry scene.

Be sure to order tickets ahead of time on their website.

Hancock Shaker Village entrance sign in Pittsfield Massachusetts

Check Out the 10 x 10 Upstreet Arts Festival

If the arts are more your style, check out the 10×10 Upstreet Arts Festival (multiple locations, Pittsfield) for things to do in the Berkshires in February.

You can expect live music, art, theater, dance, ice sculptures, and so much more at this yearly winter celebration.

With iconic events like the 10 Days of Play, the Real Art Party, and the Berkshires Jazz concert, there is so much to enjoy at the festival.

Check out the festival’s page for more information and to get schedule updates.

Bright street art in Pittsfield Massachusetts

Ski the Trails at Bousquet Mountain

Curious about night skiing?

Bousquet Mountain (101 Dan Fox Rd, Pittsfield) is a Berkshires ski area that was actually the first in America to offer night skiing.

At 1,818 feet elevation at the peak, you will love exploring all 22 trails spread across 200 acres.

Bousquet also offers high-quality rentals, lessons, and even a tuning service for all its visitors.

Make sure to stop by the LIFT BistroPub for a quick snack or a full mountainside dining experience.

Celebrate the Festival of Trees at the Berkshire Museum

The Berkshire Museum (39 South St, Pittsfield) celebrates the holiday season every year with the Festival of Trees, a beautiful display of decorated trees across the museum’s campus.

Each year’s theme is a little different, but sometimes it centers around the history and legends of Pittsfield.

Join in the holiday cheer and explore this year’s festival in December and early January.

The trees are actually set up around town, so take your family around to explore the town and enjoy the festive decorations!

Sledding at John T Reid Middle School

If you’re looking for a sledding spot that’s suitable for all ages, head to John T Reid Middle School (950 North St, Pittsfield).

The hill for sledding may not be as steep as the others but it’s great if you’re looking for a light cruise to the bottom.

Child sledding in the snow.

Ice Skate at the Boys and Girls Club of the Berkshires

The Boys and Girls Club ( 16 Melville St., Pittsfield) of the Berkshires is open to public ice skating during the winter.

They offer ice skating sessions as well as skate rentals.

Cross-Country Ski in the Berkshires at Canterbury Farm

Looking for cross-country skiing in the Berkshires?

Try your hand at the winter sport at Canterbury Farm (1986 Fred Snow Rd, Becket).

The touring center has rental skis and cross-country lessons, as well as snowshoe rentals and a frozen pond for skating (along with skate rentals).

Watch a Performance of “A Christmas Carol” at Ventfort Hall Mansion

While the Ventfort Hall Mansion (104 Walker St, Lenox) is a gorgeous wintry scene on its own, you’re able to visit and watch a performance of “A Christmas Carol” every winter.

The hall will be fully decked out for Christmas, which makes the viewing that much more festive!

Ventfort Hall Mansion was built in 1893 for J. P. Morgan’s sister.

At the time, it was a popular vacation spot in the Gilded Age, making it a historical landmark you must visit in the Berkshires this winter.

View of the Ventfort Hall Mansion and Gilded Age Museum in Lenox in the Berkshires in Massachusetts

Escape the Cold at Berkshire Botanical Garden

If the wintry weather is getting you down, duck into the warm conservatories at the Berkshire Botanical Gardens (5 West Stockbridge Rd, Stockbridge).

While the outdoor grounds close at the end of October, the Botanic Garden is still open for special events.

For even more holiday cheer, visit the gardens in early December, just in time for the Holiday Marketplace.

Shop to live music and browse one-of-a-kind holiday botanic wreaths and tons of other gift-worthy flora.

Visiting Berkshire Botanical Garden made it to our list of awesome things to do in Western Massachusetts.

Entrance and admission sign at the Berkshire Botanical Garden in Stockbridge in the Berkshires Massachusetts

View the Beautiful Winterlights at Naumkeag

The Winterlights at Naumkeag (5 Prospect Hill Rd, Stockbridge) is a fantastic and beautiful thing to do in the Berkshires in Massachusetts in winter.

Walk through the Naumkeag Gardens and enjoy the thousands and thousands of holiday lights, all designed by artists.

As you weave through the garden paths, you’ll see these lights shimmer but be sure to take caution on slippery walkways in the winter weather.

If you decide to visit the Berkshires in November, you may still be able to experience this stunning light display as it runs from around the last week of the month to early January.

The front of Naumkeag in Stockbridge in the Berkshires Massachusetts

Visit Specialty Gift Shops

If you’re thinking of more ideas on what to do in the Berkshires in winter, why not shop for the perfect holiday gift? 

The Berkshires is home to many specialty gift shops where you can do your winter shopping or see exhibits of antiques, glass art, and other crafts.

For something unique, head to Ozzie’s Glass Gallery (1670 Pleasant St, Rt.102, Lee) to watch hand-blown and sculpted glass being created on-site.

You can buy some items as a gift like glass vases, glass pens, suncatchers, jewelry, and more.

Ski the Slopes at Butternut

Skiing in Berkshires, MA is an amazing way to spend a winter vacation in the area.

Ski Butternut (380 State Rd, Great Barrington) is a well-known ski area in the Berkshires, and for good reason.

For 60 years, Ski Butternut has won awards for its prime snow conditions and beautiful mountain scenery.

You’ll love the tree-lined trails and hearty, warm meals at the lodge, so make sure you check their website for lift tickets and even mid-week discount rates!

Skate at Monterey Outdoor Ice Pavilion

For amazing outdoor winter fun in the Berkshires, visit the Monterey Outdoor Skating Rink (411 Main Rd, Monterey).

This public skating rink is simple, with no frills.

Since the conditions change on a daily basis, it is very important to check their page for updates.

Close up of someone in ice skates on an outdoor skating rink

Enjoy the Sheffield Historical Society Winter Wonderland

Looking for things to do in the Berkshires in December?

Each year, the Sheffield Historical Society (159-161 Main St, Sheffield) holds a Winter Wonderland celebration.

The celebration takes place in early to mid-December.

You can visit the Historical Society and enjoy more than 20 Christmas trees, which are ornately decorated for the holiday season.

The event is free, and kids will love meeting Santa and indulging in free snacks and treats.

There’s music, games, and other special features at this event, making it a great free thing to do in the Berkshires in winter.

Try Some Locally Made Stiff Drinks

If you find yourself needing a stiff drink to warm you up, the Berkshires boasts some of the best distilleries, breweries, and cideries in the region.

The three most notable spots to visit during your Berkshires winter getaway are Berkshire Mountain Distillers (356 S Main St, Sheffield), Bright Ideas Brewing (111 MASS MoCA Way, North Adams), and Hilltop Orchards (508 Canaan Rd, Richmond).

Snow in the Berkshires

Berkshire County averages 65 inches of snow every winter.

The average lowest temperature in January is 11 degrees Fahrenheit, but the average temperature in that month is 35 degrees.

It’s the coldest month of the year, with only December being a little warmer at 36 degrees.

Final Thoughts

Did you enjoy the activities we listed for winter in the Berkshires? Let us know your thoughts in the comments!

Leave a Reply

Your email address will not be published. Required fields are marked *