Top 15 Best Things to Do in Stockbridge Massachusetts

You’ll find plenty of things to do in Stockbridge MA, such as learning about famous artists, peeking into a Gilded Age mansion, strolling through the quaint downtown, and partaking in numerous outdoor activities.

Downtown Stockbridge Massachusetts
Photo credit: David Wilson / Flickr

A visit to the Berkshires isn’t complete without a visit to Stockbridge. This small, quaint town with a traditional New England feel is the perfect stop while exploring all that the Berkshires have to offer.

Stockbridge is nestled between two larger towns – Lenox to the north and Great Barrington to the south. But don’t let its size fool you – there are still plenty of things to do in Stockbridge MA.

Whether you’re interested in art, gardens, hiking, or exploring the town’s charming streets, Stockbridge has something for everyone to enjoy.

Spending a few hours here, or staying overnight in the town’s historic inn, is well worth it to experience what Stockbridge has to offer.

Top Things to Do in Stockbridge MA

The following are some of the best activities to add to your itinerary while in Stockbridge.

Tour the Norman Rockwell Museum

The outside of the Norman Rockwell museum - among the things to do in Stockbridge MA
Photo credit: Kerry Flatley

One of the most popular things to do in Stockbridge MA is to visit the Norman Rockwell Museum.

Dedicated to celebrating the life and works of Norman Rockwell, a renowned American painter and illustrator, the museum showcases his iconic images capturing the essence of American life between 1910 to the late 1970s.

Rockwell’s artistry resonated with millions of Americans during this time, depicting everyday scenes with humor, warmth, and poignant social commentary.

A visit to the museum will allow you to immerse in his rich collection of illustrations, including his famous Saturday Evening Post covers, as well as explore the artist’s process through his studio and archives.

Beyond appreciating Rockwell’s talent and storytelling ability, you’ll also leave the visit with a deeper understanding and appreciation of American culture.

Tickets purchased online in advance come with a discount. See the website for more details. The museum is open every day except Wednesdays and select holidays. (9 Glendale Road)

Peek into the Gilded Age at Naumkeag

The outside of Naumkeag mansion
Photo credit: Kerry Flatley

Explore the Gilded Age lifestyle of an affluent family during a visit to Stockbridge MA’s Naumkeag estate.

This 48-acre property was commissioned by Joseph Choate, a prominent New York lawyer and U.S. ambassador to Great Britain, who, with his wife, built Naumkeag as a summer retreat in the late 19th century.

The house features 44 rooms and showcases a blend of architectural styles, including Shingle Style and Queen Anne. Several generations of the Choate family lived at Naumkeag until daughter Mabel Choate bequeathed it to The Trustees in 1958.

After touring the house, wander among the property’s gardens which include terraced lawns, elegant flower beds, a Chinese Garden, and a stunning Blue Steps feature.

Naumkeag is opened seasonally. Check the website for hours and secure your spot on a tour on the website. (5 Prospect Hill Road)

Experience the Berkshire Botanical Garden

White and yellow flowers at the Berkshire Botanical Garden
Photo credit: kathryn / Flickr

Garden lovers will want to make time to walk amongst the flora and fauna at the Berkshire Botanical Garden. This beautiful garden showcases a diverse collection of plant species and features various themed gardens, including a rock garden, herb garden, and woodland garden.

Established in 1934, this tranquil oasis is thought to be one of the older public display gardens in the Northeast. The 24-acre property emphasizes plants that are native to the region and features a topiary garden of animals and “live” sculptures.

Several major events happen at the garden throughout the year including Harvest Festival, Winter Lecture, a plant sale, and Fête des Fleurs Garden Gala, to name a few.

A map of the gardens can be viewed here. The garden is open from April 29th – October 31st, from 9 AM to 5 PM. General admission is $18 and children 12 and under are free. A few other discounts apply – see the website for more details and to confirm dates and prices. (5 West Stockbridge Road)

Explore Chesterwood and learn about Daniel Chester French

Chesterwood - a home in Stockbridge Massachusetts

A visit to Chesterwood in Stockbridge, MA, is a must for admirers of American sculpture and those interested in the life and works of Daniel Chester French (1850-1931).

French, a renowned American sculptor, is best known for his creation of the seated statue of Abraham Lincoln at the Lincoln Memorial in Washington, D.C..

He also created Minute Man, a statue erected in front of Concord, Massachusetts‘s Old North Bridge to commemorate the centennial of the Revolutionary War.

Chesterwood, French’s former summer home and studio, showcases a collection of French’s sculptures, including maquettes, studies, and larger works, allowing visitors to witness the evolution of his artistic vision.

Additionally, the serene and picturesque surroundings of Chesterwood provide a tranquil setting for exploration, making it an ideal destination for art enthusiasts and nature lovers alike.

Chesterwood is open from the middle of May to the middle of October. During that time it’s open daily from 10 AM to 5 PM but is closed on Tuesdays. General admission is $20 with discounts available for select individuals. Check the website for specific dates and to confirm times & prices. (4 Williamsville Road)

Wander through Stockbridge’s historic downtown

A street scene from historic main street in Stockbridge MA
Photo credit: Kerry Flatley

Stockbridge has a small but charming downtown that’s easily walkable. Wandering down Main Street, you’ll be surrounded by a mixture of historic New England architecture creating the sense of stepping back in time.

Among the best things to do in Stockbridge MA’s downtown is to step inside the William and Son’s Country Store. A visit here will make you feel you’re no longer in the 21st century with its wooden floors, barrels holding toys and gifts, and shelving with the quaintness of a different era. (40 Main Street)

If you’re looking for a quick bite to eat, be sure to stop in the Main Street Cafe next door for breakfast or lunch. Located in the old Stockbridge General Store building, you’ll find American culinary favorites here in a cozy setting. (40 Main Street)

And finally, if you’re looking for the perfect gift, or just want something to remember your trip by, stop in to Sidetracks. Here, you’ll find everything from apparel, puzzles, cards, kitchen supplies, and home goods. (8 Elm Street)

Hike the Ice Glen and Laura’s Tower

Rocks, boulders, and trees along the Ice Glen hike
Rocks, boulders, and trees along the Ice Glen hike

Experience the natural beauty of Stockbridge by hiking the Ice Glen Trail and continuing on to Laura’s Tower Trail leading to the summit of Laurel Hill.

This moderately challenging trail leads through impressive rock formations and forest views. And a continuation up Laura’s Tower trail leads to a metal tower at the summit with panoramic views of the Berkshires, including Mount Greylock in the north.

Laura’s Tower Trail is about 1.8 miles and is considered moderately difficult. The Ice Glen trail is 1.4 miles out and back and is considered difficult due to the need to climb and navigate boulders.

The Ice Glen Trail can be accessed at the end of Park Street near downtown Stockbridge or just off of Ice Glen Road. Laura’s Tower Trail bisects the Ice Glen Trail about halfway up.

Stay at the Red Lion Inn

The outside of the Red Lion Inn in Stockbridge MA
Photo credit: Daderot / Creative Commons

If you enjoy staying in old, quaint inns, you’ll enjoy The Red Lion Inn – a historic landmark built in 1773 and located at the heart of downtown.

Much of this inn’s original character has been preserved, including furniture and a few antique items such as the old switchboard and elevator. There’s also a pool on the property for guests. And anyone – guests and visitors – can eat dinner at the inn’s restaurant or shop in the gift store.

The Red Lion’s property includes the original Main Inn, a more contemporary 17-room guest house, and a few other lodging options including an early 20th century Firehouse. (30 Main Street)

Spend time at the Stockbridge Bowl

The Stockbridge Bowl in the wintertime

If you enjoy spending time on the water, be sure to visit the Stockbridge Bowl, also known as Lake Mahkeenac, a 372-acre artificially impounded body of water.

This is the largest lake within the town of Stockbridge and is a popular spot for swimming, kayaking, paddleboarding, or picnicking by the water’s edge. The northern end of the lake is overlooked by Tanglewood in Lenox, the summer residence of the Boston Symphony Orchestra.

The lake is just shy of two miles long and about three-quarters of a mile wide. It’s open to the public year-round.

Catch a show at the Berkshire Theatre Group

If you’re in the mood for a bit of entertainment while in Stockbridge, be sure to catch a performance at the Berkshire Theatre Group.

While the Berkshire Theatre Group has a number of stages, its Unicorn Theater (6 East Street) and Fitzpatrick Main Stage (83 East Main Street) are located right in the heart of Stockbridge. Both offer a variety of theater productions, including plays, musicals, and concerts.

Check the website to see which shows are available while you’re visiting. Tickets can be purchased online or at the box office.

Explore the Stockbridge Library, Museum & Archives

If you enjoy local history, you’ll want to make a stop at the Stockbridge Stockbridge Library, Museum & Archives, housed in a historic building on Main Street.

Here, you’ll discover its collection of books, manuscripts, artwork, and local artifacts that showcase the town’s history. You can also pick up a map of the local cemetery across the street.

This library was founded in 1862 and is one of the earliest libraries established in western Massachusetts. (46 Main Street)

Visit the Stockbridge Summer Arts and Crafts Show

If you’re visiting Stockbridge in the middle of August, you’ll want to make time to check out The Stockbridge Summer Arts and Crafts Show.

This much-anticipated event showcases the talent and creativity of local and regional artisans and attracts a wide range of artists and craftspeople.

With over 100 exhibitors, you can expect to see a diverse array of artwork, crafts, and handmade goods. From paintings, sculptures, and photography to jewelry, ceramics, and textiles, there is something for every artistic taste.

The show provides a unique opportunity to meet the artists, learn about their techniques, and even witness live demonstrations. (50 Main Street)

Relax at the Kripalu Retreat

A calming thing to do in Stockbridge MA is to head over to the Kripalu Center. For more than 50 years, this retreat has offered yoga and mindfulness-based education.

While the Kripalu Center has many retreats throughout the year, its signature offering is The Kripalu R&R Experience. This individualized experience allows visitors to book either a day pass or opt to stay overnight.

Included in the experience is the ability to book multiple yoga, dance, movement, Ayurveda, and other classes, eat three all-natural meals, partake in spa treatments and meditation sessions, and access more than 100 acres of hiking trails, walking paths, and a lakefront.

See the website for more details and learn how to sign up for a retreat. (57 Interlaken Road)

Pick up some local produce at the West Stockbridge Farmer’s Market

A hand reaching over produce to give a buyer an apple for purchase at a farmer's market

If you’re visiting Stockbridge in the summer or fall, don’t miss the West Stockbridge Farmers Market. Although West Stockbridge is technically a separate town, it’s only a short drive west from downtown Stockbridge.

This market, located on the Foundry Green, offers a combination of fresh local produce, artisanal goods, and live music. You’ll find a wide selection of meats, cheeses, vegetables, fish, bread, ice cream, baked goods, jams, and maple syrup among other offerings.

The farmer’s market takes place from the middle of May to the beginning of October on Thursday afternoons. Check the website for more details. (Harris Street, West Stockbridge)

A photo of Kerry Flatley leaning against a wall

About Kerry Flatley

Kerry Flatley has lived in New England for the past 26 years. She has roots in Maine & Massachusetts, family in New Hampshire, and grew up close to the Connecticut border. She loves all that this region has to offer – the ocean, mountains, islands, history, villages, and cities. When she’s not writing about New England, she’s relaxing at home in the Boston suburbs with her two teenage daughters and husband.

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