School Break? Spend it in Great Barrington
Looking for a fun and engaging way to spend school break with the whole family? Whether it’s February vacation or a winter long weekend, Great Barrington offers the perfect mix of outdoor adventure, culture, and cozy downtime to keep everyone entertained.
From skiing and snow play to museums and family-friendly dining, here’s how to make the most of your time in the Berkshires this winter.
Explore the Great Outdoors
School break is the perfect excuse to get outside—and in the Berkshires, winter only adds to the fun. With snow-covered landscapes and fresh mountain air, there’s no shortage of ways to stay active.
If your family loves skiing (or wants to try it for the first time), Ski Butternut is just minutes away and offers approachable terrain for all skill levels, plus snow tubing that’s always a hit with kids.
Prefer something a little slower-paced? Head out for a winter hike on local trails like Monument Mountain or explore nearby paths in Beartown State Forest. Snowshoeing and simple snow play can be just as memorable as a full day on the slopes.
Experience Local Culture
The Berkshires are known for their vibrant arts and culture scene—even in the winter months.
Catch a family-friendly performance at the Mahaiwe Performing Arts Center, where programming often includes live music, film, and special events.
For a hands-on indoor experience, take a short drive to Berkshire Museum. This interactive museum features an aquarium, art galleries, and the “Curiosity Incubator,” making it a great option for kids of all ages—especially on colder days.
Dine Family-Style
After a day of exploring, you’ll definitely have some hungry kids on your hands. Luckily, Great Barrington has plenty of family-friendly dining options.
A local favorite, Baba Louie's serves up wood-fired pizzas, fresh salads, and comforting, crowd-pleasing dishes that even picky eaters will love.
You’ll also find plenty of casual cafés, bakeries, and takeout spots throughout town—perfect for easy, flexible meals between activities.
Stay & Unwind at Little Lion Inn
When it’s time to settle in, make <a href="/little-lion-inn">Little Lion Inn</a> your home base for school break. Just minutes from downtown Great Barrington and close to top attractions, it’s an easy, comfortable place to land after a full day of adventure.
Our rooms are designed with families in mind—and yes, pets are welcome too (with no pet fees). In the evenings, unwind by the fire pit, relax in our cozy common spaces, or enjoy some downtime with games and movies.
Plan Your Winter Getaway
A school break in the Berkshires is all about balance—fresh air, creative experiences, and time together as a family.
Book your stay at Little Lion Inn and start planning a winter escape your kids (and you) will actually remember.