Things to Do in Stockbridge, Massachusetts

Steeped in rich history and culture, the idyllic town of Stockbridge is renowned for art museums and galleries and historic homes and gardens. It's a must-visit for anyone interested in the wonders of Western Massachusetts. In this article, we'll share some of our favorite awe-inspiring attractions. 

Contact us today!

Norman Rockwell Museum

Named the most popular year-round cultural attraction in the Berkshires, the Norman Rockwell Museum displays nearly 1,000 original works from the renowned painter and illustrator, who lived in Stockbridge for the last 25 years of his life. The Museum also houses the Norman Rockwell Archives, a collection of more than 100,000 items, including working photographs, letters, personal calendars, fan mail, and business documents.

The Mission House

A National Historic Landmark, The Mission House tells the story of the Stockbridge Mohicans. Built by missionary John Sergeant on Prospect Hill, the house watched over Stockbridge for nearly 200 years before Mabel Choate preserved it and moved it to its present location on Main Street. Today, it serves as a museum filled with a collection of colonial American furnishings and indigenous objects. 

Chesterwood 

Tucked away in the Berkshires sits the former summer home of 20th-century sculptor Daniel Chester French. Best known for The Minute Man in Concord, MA, and the seated figure of Abraham Lincoln in Washington, DC, French earned the laurel "master of his medium.” He built Chesterwood, a beautiful retreat in Stockbridge, to resemble a Gilded Age sanctuary. The property, which he referred to as "a piece of heaven on earth," spans 122 acres and features the residence, an artist studio, and lush garden landscapes. Visit this historic site and experience the life and work of this prolific public figure.

Naumkeag

Located in the heart of the Berkshires, Naumkeag wows with its 44-room historic house and eight acres of gardens. Stop by the beloved blue steps, a double stairway with white-arched, blue-painted grottoes, or grab high tea at the Rose Garden Café. If you plan your visit right, you can indulge in activities, from sunset yoga to wine walks, with a backdrop of Monument Mountain and the Housatonic River Valley.

Berkshire Camino

Inspired by the Camino de Santiago in Spain, Berkshire Camino curates guided hiking retreats for those who want to experience the area's beauty on foot. From town walkabouts to woodland hikes, participants can gain a sense of connection to others and the community as they mindfully traverse these natural trails. Get your packs ready and explore the history, culture, flora, and fauna around you.

Berkshire Botanical Garden

The Berkshire Botanical Garden boasts 24 acres of native Northeast plants. From perennial borders to seasonal scapes, stroll through a sanctuary awash in color all year. Want company? Opt for a self-guided audio tour presented by Grace Angela Henry. You can enjoy a tranquil afternoon by the pond garden, walk down the daylily path, see over 100 varieties of herbs, and delight in custom-designed topiaries with captivating vignettes. 

Williams & Sons Country Store

Situated on Main Street in Stockbridge, Williams & Sons Country Store is amassed with unique gifts and souvenirs. A staple since 1790, this old-fashioned, family-owned and operated shop brings small-town vibes to the Berkshires. Treat yourself to jams, jellies, honey, teas, penny candy, candles, postcards, soaps, fire cider, and more.

7 Arts Music

Audiophiles, rejoice! 7 Arts Music on Main Street stocks a variety of vintage vinyl records, CDs, cassettes, and more. Whether you're looking for a limited-edition album or prefer to browse the bins in search of your next favorite sound, 7 Arts Music is a can't-miss stop. 

Peace, Love, and Chocolate

Need a sweet treat after your journey around Stockbridge? Stop by Peace, Love, and Chocolate, a neighborhood cafe and coffee house specializing in gourmet coffees and handmade candies. Try one of their seasonal truffles or milk chocolate malt balls. 

STay at the Red Lion Inn

There are endless places to explore in Stockbridge throughout the year. From casual outdoor rendezvous to historic sites, complete your tour around town at Red Lion Inn, a landmark of hospitality for 250 years. The best of the Berkshires awaits. Book your stay now.

Previous
Previous

Dining in Stockbridge, MA: Our Favorite Restaurants in the Area

Next
Next

Where to Find the Best Christmas Lights Around Stockbridge, MA