Outdoor Winter Fun in the Berkshires

Looking for winter fun in the Berkshires? Here's our list of can't-miss family fun.

By Berkshires Macaroni Kid January 3, 2024

We're all looking for ways to get out of the house in the Berkshires this winter! Fresh air is good for the soul — not to mention it helps to get the wiggles out of the kids. So we put together a list to help you find fun things to do this winter with your family in Berkshire County during these next few winter months: 

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1. Snowshoe or cross country ski at Notchview in Windsor

With more than 3,000 acres of rolling terrain and miles of groomed ski trails, Notchview, a part of the Hoosac Range in the Berkshire Hills, offers an idyllic escape all year round—but especially in winter. Day & Season Passes Available, Ski & Snowshoe Rentals on site. *Update: We are still waiting for enough snow to open for the season. Hours of operation are 8:30 a.m. to 4:30 p.m. Please check snow report for daily weather and grooming updates.

2. Go Snow Tubing 

Whether you hit up Bousquet in Pittsfield, Jiminy Peak in Hancock, or Ski Butternut in Great Barrington, an afternoon of tubing is guaranteed fun for the whole family. Just make sure to book your tubing passes in advance, they sell out fast!

3. Go Sledding

They don't call it the Berkshire hills for nothing and we've got no shortage of great sledding locations (when there's snow!) Check out this list of our favorite local sledding hills and bookmark it for the next snow day!

4. Go Ice Skating

When the weather allows, the Berkshires has many ponds, lakes, and man-made skating locations. There are even a few indoor rinks open for lessons, free skate, hockey, and more! Check out our list of ice skating spots, HERE.

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5. Go Ice Fishing

Once the real winter cold sets in, ice fishing takes center stage (hopefully!) Check out this list of upcoming derbies and tournaments, but be aware that most have not been scheduled yet for 2024 and are contingent on the weather.

6. Take a Winter Hike

Don't let the winter stop you from hitting the trails! There are a ton of easy winter hikes to be found in the Berkshires and bonus — no bugs! Check out Berkshire Natural Resources Council for a great list of trails and events, Berkshire Family Hikes' List of Winter Hikes for Families, and Mass Audubon Pleasant Valley for events and more!