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Things to do in The Berkshires: Top Activities

Nestled away in the hills of western Massachusetts are The Berkshires, one of the state’s most beautiful and underrated regions.

This area is a unique blend of historical sites, outdoor adventures, and charming small towns that will complete your New England experience. From catching live music to exploring art galleries — there’s something for everyone in The Berkshires.

However, that much splendor brings about indecision, especially if you’re pressed for time. What do you do? What do you not do? Well, no need to worry anymore, this guide will help you narrow down what activities to do while in the Berkshires without feeling guilty that you missed out on any others.

Where to Stay in the Berkshires

There are so many things to do, so you’ll want to book a night or two of accommodation to see it all. To ensure you have the best time possible, book one of the following comfortable accommodations.

Stockbridge Country Inn

As the name may suggest, the Stockbridge Country Inn is located in Stockbridge, Massachusetts. This incredible bed and breakfast features lovely suites, a breakfast menu to get the day started right, beautiful gardens, and a fantastic pool for a peaceful stay.

It also boasts a convenient location that’s closest to some of the town’s best attractions, like the Norman Rockwell Museum, and it’s near the Tanglewood music venue.

Cost: From $299 per night


If you’re a traveler with a love for luxury, the Wheatleigh should be among your top choices. One of the leading small hotels in the world, the luxurious property features spacious suites with views of the mountain in the Berkshires. Before heading to any of the above attractions, start your day with gastro-bistro-inspired fare at The Bistro between Wednesdays and Sundays.

Cost: From $701.54 per night

Top Berkshires Activities

Let’s not waste any more time; here are the Berkshires’ best things to do.

Tip: If you’ve got more time, consider exploring some of the more unique things to do in New England.

Catch Live Music at Tanglewood

Tanglewood Concert


If music is what gets your heart pumping, then you won’t find any place better than Tanglewood in Stockbridge. This music venue, which is an outdoor concert spot, has been a summer favorite for music lovers all over the world since the mid-1930s.

The sprawling green lawns, rolling hillsides, and majestic trees make for a surreal setting that only adds to the charm of the music. While there isn’t a set list of performers, the names that headline the shows are always a draw, as artists like Whitney Houston, Bob Dylan, and The Black Crowes have previously taken to the stage.

Wander Around the Lakes

The Berkshires is a wonderland of natural beauty, so it’s no surprise that the region is home to a collection of serene and stunning lakes. Spend your time here by jumping into the waters, enjoying a peaceful kayaking experience, or setting up a picnic while admiring the forestry that calmly reflects off the waters.

You can certainly come whenever, but you’ll have the most fun during fall when the surrounding greenery features orange and red hues. There’s an extensive number of lakes to go to, but many don’t compare to Lake Buel, Queechy Lake, and Otis Reservoir.

Shopping in Lenox

Woman shopping

When it comes to shopping, Lenox offers a unique and charming experience. The town’s historic streets are lined with quaint boutiques and specialty shops, each one radiating character and warmth.

Among the best places to shop here is the Catwalk Boutique, which sells upscale women’s clothing that will add pizzazz to any wardrobe. If you prefer bling, then the Concepts of Art is the perfect place to grab jewelry.

Explore the Berkshire Museum

If you’re looking for a cultural hotspot in western Massachusetts, look no further than the Berkshire Museum. Nestled in the picturesque town of Pittsfield, this museum offers visitors a chance to explore the intersection of art, science, and history.

Among the museum’s diverse range of 40,000-plus exhibits is the Feigenbaum Hall of Innovation, which details the many notable residents of the Berkshires. If learning about Berkshires royalty isn’t enough, discover the many creatures that call the region home at the Berkshire Backyard.

If you’re an art lover, you have to stop by the Objects and Their Stories exhibit. As the newest addition to the museum, it takes you on a journey across time via several sculptures, paintings, and more.

Marvel at the Art at the Massachusetts Museum of Contemporary Art

MASS MoCA Exhibit by Louise Bourgeois


The Berkshire Museum wasn’t enough to fill your hunger for arts? No worries, the Massachusetts Museum of Contemporary Art (MASS MoCA) awaits in North Adams.

MASS MoCA is a 250,000-square feet space of nothing but contemporary art that will surely leave you gasping in awe. Among the works of art on show here are interactive exhibitions, incredible sculptures, beautiful paintings, and fantastic ceramics.

That’s not all, though; the art haven also plays host to the performing arts. It had performances from bubbling artists like Rina Sawayama, Danielle Ponder, and more.

Visit The Mount

Bibliophiles might not have a better place to visit in the Berkshires than The Mount. This property, which was the home of author Edith Wharton, is a must-see destination for anyone who appreciates her writing exploits.

Visitors can explore the beautifully preserved rooms and gardens that inspired Wharton’s writing, gaining insight into her life and legacy. There are a number of exhibits that focus on both her writing and personal life, which can help fans get a deeper understanding of her literature.

Final Thoughts on The Best Things to Do in the Berkshires

Pittsfield Lake

Well, there you have it — a few of the amazing activities you can do in the Berkshires. From shopping and viewing art to live performances, there’s truly something for everyone here. The Berkshire region serves as an ideal destination for those looking to explore nature, learn new things, and enjoy the beauty of Massachusetts.

Tip: No need to bring a number of bags with you; check out this guide on packing hand luggage like a pro.

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