Top Things To Do While Visiting The Berkshires

Looking for things to do when you visit the Berkshires? Here is our top list of things to do while visiting the Berkshires.

Berkshire East

Zip Line Canopy Tours

With three different zip line canopy tours featuring some of North America’s longest zip lines, Berkshire East Canopy Tours is New England’s largest zip line destination. Featured by USA Today as one of the top 10 zip lines in the United States! Whether you are getting a taste of zipping on our Base Area Tour or seeking an adrenaline rush on our Valley Jump, there is something to suit all interests. Each tour has limited space, so make sure to make a reservation in advance.

Mass MoCA Museum

MASS MoCA is one of the world’s liveliest centers for making and enjoying today’s most evocative art. With vast galleries and a stunning collection of indoor and outdoor performing arts venues, MASS MoCA is able to embrace all forms of art: music, sculpture, dance, film, painting, photography, theater, and new, boundary-crossing works of art that defy easy classification. Much of the work we show in our light-filled spaces, on our technically sophisticated stages, and within our lovely network of late 19th-century courtyards is made here during extended fabrication and rehearsal residencies that bring hundreds of the world’s most brilliant and innovative artists to North Adams all year round.

The Berkshires Fall Foliage

The Berkshires fall foliage season begins late September and typically peaks during mid-October, Columbus Day weekend. If you’ve a love for forested backdrops of crimson, yellow, russet, and all tones in between, a Berkshires fall foliage trip is for you!

Speaking of views, if you’ve made it to North Adams on your Berkshires fall foliage drive, you may as well summit Mount Greylock. You won’t need any carabiners or crampons to make it, though – you can drive there!

Mount Greylock is 3,491 feet tall: the highest point in Massachusetts. From its peak on a clear day, you can see more than 90 miles away. That’s a LOT of leaf-peeping! Stop by the cafe at rustic Bascom Lodge for a prix-fixe dinner and vistas of four states and five mountain ranges.

Ozzie’s Glass Gallery

Custom memorable glass-blown pieces. Spend some time looking for the perfect piece of art for your home. If you plan your visit to Ozzie’s – you might just catch him working over fire creating these one of a kind items.

Located on Rt 102 in Lee, MA.

“Beautifully designed jewelry and gifts. And just a great guy! We enjoyed our visit to your shop. And I love my angel wing necklace.”

Hiking In The Berkshires

Olivia’s Overlook/Yokun Ridge trail – One of the most scenic views in the Berkshires, Olivia’s Overlook provides stunning vistas of Stockbridge Bowl. A MUST for family photos and selfies. Just across the street is the Yokun ridge trail, which leads up to views of the overlook in one direction, and to the quiet, picturesque Monk’s Pond down the other. This hike is perfect for an easy in and out day hike and is ideal for families.

The Cobbles – Is an easy day hike located in Cheshire, MA. The trail leads to a breathtaking view of Cheshire Lake and surrounding mountains. Perfect for families with wearable and/or older children, the in and out trail is around 2 miles long and crosses the Appalachian Trail along the way.

Berkshire Mountain Distillers

While you are in the Berkshires, be sure to take the time to head to Sheffield and get your Berkshire Mountain Distillers tour. Smell the hopps and see how all their products are created. Stop by their store (don’t all tours or rides end in a gift shop?) and pick up a bottle or two of their products. I’m a big fan of their Bourbon Whiskey.

Founded in 2007, Berkshire Mountain Distillers (BMD) has grown to include a wide range of award-winning spirits: Ice Glen Vodka, Greylock Gin, Ethereal Gin, Ragged Mountain Rum, Berkshire Bourbon and New England Corn Whiskey. Chris began selling BMD’s spirits door to door in Massachusetts out of the back of his truck, and today BMD is available in 19 states. Chris remains fully involved at the distillery and has a passionate hands-on relationship with every bottle. His current role as owner and distiller is an amalgamation of his passions: farming, chemistry, and construction.

Canyon Ranch – Lenox

Here, you’ll find an inviting and supportive space to energize and navigate your own wellness. Dine on locally-sourced cuisine, challenge yourself with kettlebells or dance class. Relax in saunas, steam rooms, and whirlpools. Take in the beauty of nature on guided outings. Feel tension melt in a signature massage or ayurvedic treatment.

Choose a curated experience pathway and meet with experts in medicine, exercise, nutrition, or spirituality working together to help you achieve optimal health. Or just be here, to begin your new path to wellness among the healing mountains.

From simple group getaways, to celebrations, reunions, business meetings and retreats, Canyon Ranch Lenox offers the outdoor activity and shared wellness experiences to bring you together like nowhere else.

Zoar Outdoor – Charlemont MA

Why Raft with Zoar Outdoor?
Nothing promotes teamwork like paddling together down a class III rapid. Nothing enhances connections like spending a day working in unison to avoid obstacles or challenging waves. Nothing relieves stress like being outside, focusing on the river and experiencing excitement!

Gather your friends or family and head to Charlemont MA – Zoar Outdoor will take care of all the gar. You just dive in and experience the thrill. Raft down the Deerfield River. Get wet, be involved and even learn a thing or two about yourself. Their friendly and professional guides will be there every step of the way.

Williamstown Theatre Festival

Williamstown, MA

Founded in 1954 by Nikos Psacharopoulos, the Tony Award-Winning Williamstown Theatre Festival is regarded as one of the great summer stock companies in the US; and has successfully transferred more than 5 productions to Broadway.

Berkshire Theatre Group

Stockbridge/ Pittsfield, MA

Founded in 1928, Berkshire Theatre Group is one of the oldest and most loved theatre companies in the Berkshires. On three stages, BTG has produced over 550 plays and musicals featuring such actors as James Cagney, Lionel Barrymore, Lillian Gish, Katharine Hepburn, and Buster Keaton.

Barrington Stage Company

Pittsfield, MA

In 1995 Barrington Stage opened its doors at the former Union Square Theatre on Union Street. BSC is known for producing new plays and musicals, including the two-time tony winning musical “The 25th Annual Putnam County Spelling Bee.”

Mac Haydn Theatre

Chatham, NY

In 1969 the Mac Haydn Theatre opened its inaugural season with My Fair Lady in a rented barn. Since then, they’ve upgraded to their own space and have welcomed thousands of audience members and hundreds of NYC actors, producers, and set designers; including the fabulous Nathan Lane.

Mixed Company Theatre

Great Barrington, MA

Mixed Company Theatre was founded in 1982 and is Berkshire County’s oldest year-round theater. Mixed Company-a non-profit, 501-c-3 theater and state-of-mind. Cofounded by playwright Joan Ackermann & Gillian Seidl.

Mahaiwe Performing Arts Center

Great Barrington, MA

Since first opening as a vaudeville theatre in 1905, the Mahaiwe Performing Arts Center has been the pinnacle of Performing Arts Venues in the Berkshires. It’s the Berkshire home to many Broadway stars from Patti LuPone and Mandy Patinkin to Jason Daniely and the late Marin Mazzie.

GhostLit Rep Company

Egremont, MA Great Barrington, MA

A new theatre company in Berkshire County that strives to innovate and celebrate transformative work, from the odd and experimental to the classic musical. Their main performance spaces are The Barn in South Egremont and Saint James Place in Great Barrington.

Norman Rockwell Museum

Stockbridge, MA

The Norman Rockwell Museum houses the largest and most significant collection of Rockwell’s work. Many items in their collection were created and inspired by the surrounding Berkshire scenery and communities – something fun to explore for visitors of every age. The museum also features all of Rockwell’s Saturday Evening Post covers and welcomes visitors to explore his Stockbridge studio. In addition to being a world-class art museum, the Normal Rockwell is also a lovely setting for weddings and special events. Situated on over 40 scenic acres, the Museum has a seasonally tented terrace ideal for a formal reception and sweeping vistas perfect for an unforgettable wedding ceremony.

Hancock Shaker Village

Pittsfield, MA

Hancock Shaker Village has the largest collection of Shaker artifacts available at an original Shaker site. Featuring pristinely restored Shaker buildings, HSV also boasts beautifully manicured heirloom vegetable gardens and a robust working farm. Visitors to the museum can tour the iconic Round Stone Barn, visit a barnyard full of animals, and learn how Shakers practiced woodworking and oval box making – just to name a few things. A visit to Hancock Shaker Village is certain to be fun for the whole family!