Things to Do in Great Barrington, MA
When it comes to things to do in Great Barrington, Massachusetts, you’ll find no shortage of charm, culture, and outdoor adventure. Nestled in the heart of the Berkshires, this vibrant town offers a thoughtful mix of scenic hikes, performing arts, local shops, and standout dining that make it a destination worth exploring year-round. Here’s how to make the most of your time in Great Barrington.
Monument Mountain
One of the Berkshires’ most iconic hikes, Monument Mountain offers breathtaking views paired with a rich literary history—this is where Nathaniel Hawthorne and Herman Melville once found inspiration. The most popular route is a moderate 3-mile loop, winding through forested trails to dramatic cliff overlooks with sweeping views of the Housatonic River Valley. It’s the perfect blend of nature, exercise, and local lore—and just minutes from town.
Post-hike tip: Refuel in town with a casual bite at The Bistro Box or enjoy a more elevated, farm-to-table meal at Prairie Whale.
Mahaiwe Performing Arts Center
For a taste of culture and entertainment, head to the Mahaiwe Performing Arts Center. This beautifully restored historic theater has been a local favorite since 1905, hosting a wide range of performances including live music, theater, dance, film, and comedy. Whether you’re catching a nationally touring act or a more intimate performance, the Mahaiwe is a cornerstone of the Berkshires arts scene.
Make a night of it: Pair your show with dinner at Pizzeria Boema for wood-fired pizza or Frankie’s Ristorante for classic Italian.
Bernay Fine Art
Located in the heart of downtown Great Barrington, Bernay Fine Art showcases a curated collection of contemporary works by regional and nationally recognized artists. With a range of styles and mediums—from painting and sculpture to mixed media—it’s an inviting space to explore and discover something new.
Nearby: Grab a coffee or light bite from one of the many local cafés just steps away.
Lauren Clark Fine Art
Housed in a charming Victorian-era building, Lauren Clark Fine Art features rotating exhibitions from both emerging and established artists. The gallery offers a dynamic and immersive experience, making it a must-visit for those looking to engage with the Berkshires’ thriving arts community.
The Appalachian Trail
Great Barrington offers easy access to the Appalachian Trail, making it a prime destination for hiking in the Berkshires. Nearby access points—including sections through Beartown State Forest—allow for everything from short scenic walks to more challenging day hikes. No matter the season, the natural beauty of the region is always on display.
After your hike: Cool down with a drink at a local brewery or head back into town for a relaxed meal.
Cove Bowling Alley (Cove Lanes)
For a more laid-back outing, Cove Bowling Alley is a longtime local favorite. This retro-style bowling spot offers classic lanes, a lively atmosphere, and a fun option for families, couples, or groups looking for something a little different.
Keep the fun going: Plan dinner nearby and turn it into a full night out.
Independent Bookstores
No New England town is complete without a cozy bookstore. Spots like Familiar Trees Bookshop offer a welcoming space to browse new releases, literary favorites, and thoughtfully curated titles. It’s the perfect place to slow down and spend a quiet afternoon.
Perfect pairing: Pick up a book, then settle in at a nearby café for a relaxed afternoon.
Fluff Alpaca
A standout for shopping in Great Barrington, Fluff Alpaca is known for its luxuriously soft, beautifully crafted garments and accessories. From sweaters and scarves to gifts and home items, everything is made from premium alpaca fiber—perfect for bringing a bit of Berkshire comfort home with you.
Elise Abrams Antiques
For vintage lovers, Elise Abrams Antiques is a must-visit. This expansive, eclectic shop features a wide range of antique furniture, collectibles, artwork, and one-of-a-kind décor pieces. It’s the perfect place to hunt for a unique find with history and character.
Stay at Little Lion Inn
With its blend of outdoor beauty, arts and culture, shopping, and dining, Great Barrington is a Berkshires destination you’ll want to return to again and again. Whether you’re hiking Monument Mountain, exploring local galleries, or enjoying a night out, there’s something here for everyone.
Make your stay even more memorable at Little Lion, a cozy, pet-encouraging retreat just minutes from it all (and with no pet fees). With thoughtfully designed rooms and easy access to the best of the Berkshires, it’s the perfect home base for your getaway.
Explore our offers to start planning your stay.