Top 15 Best Things to Do in Lenox Massachusetts

You’ll find plenty of things to do in Lenox, MA, a small town that hosts Gilded Age mansions, houses a world class orchestra in the summer, and features numerous artistic and outdoor events and recreation.

Stores in Lenox MA
Photo credit: WalkingGeek / Flickr

Looking for things to do in Lenox, MA? You’ll find plenty in this small town that’s teeming with artists, cultural activities, and events.

During the early 1900s, Lenox was referred to as the “Newport of the Berkshires” since wealthy industrialists from Boston and New York City would spend their summers here, including relatives of the Morgans, Astors, and Vanderbilts. Many of them built “cottages” in Lenox transforming it into a fashionable summer resort destination and bringing their interest in the arts and culture with them.

Many of those “cottages” – often thirty plus room mansions built on twenty acres – still stand today but are used as hotels or museums rather than secondary residences.

And the arts scene is as vibrant as ever both here in Lenox and throughout the Berkshires. Theater, visual art, and music are all celebrated and easily accessible – both through paid and free opportunities.

15 of the Best Things to Do in Lenox, MA

So without further ado, here are some of the best things to do during your time in Lenox, MA.

Take in a concert at Tanglewood

Tanglewood, the summer home of the Boston Symphony Orchestra (BSO), is the crown jewel of Lenox and a major attraction.

This outdoor amphitheater allows visitors to listen to music while sitting or picnicking outside, surrounded by the picturesque Berkshire hills.

While performances by the BSO are the primary focus of Tanglewood, the season features a diverse range of classical music, contemporary performances, POPS concerts, and music festivals.

Tanglewood’s main performance season runs from late June to early September and tickets can be purchased online.

Looking for something more casual and less expensive than a standard BSO performance? Be sure to check out the BSO’s Saturday morning rehearsals beginning at 10:30 AM and lasting about 2-3 hours. (297 West Street)

Explore The Mount

The outside of The Mount, a white mansion in Lenox MA

One of the more intriguing things to do in Lenox MA is to visit The Mount, the former estate of author Edith Wharton.

Built at the turn of the 20th century, this mansion and surrounding gardens exemplify the architectural and cultural style of the Gilded Age – including the building’s grandiose design, opulent interiors, and meticulously landscaped gardens.

Wharton, a prominent figure of her time, used The Mount as a gathering place for the literary and social elite, contributing to the vibrant cultural scene of the era. Tours of the estate provide insights into Wharton’s life and work, showcasing the Gilded Age architecture and decor that inspired her writing.

Visitors can opt for either a self-guided tour or a guided tour. Guided tours frequently sell out and advanced purchase is recommended. Also available are private library tours and ghost tours. (2 Plunkett Street)

View the SculptureNow exhibit

An outside sculpture of a deer
Photo credit: Kerry Flatley

If you happen to be in Lenox from the beginning of June to mid-October, a fun and free way to experience art is to explore the SculptureNow exhibit.

This exhibit, which for the past 10 years has been featured on the grounds of Edith Wharton’s home The Mount (see above), showcases the sculptures of 20-30 regional, national, and international artists.

The event is free to the public and available from dawn to dusk. An audio guide and sculpture map are available at The Mount’s ticket booth. (2 Pluckett Street)

Stroll through Lenox Village

Buildings in downtown Lenox MA
Photo credit: Kerry Flatley

A visit to Lenox isn’t complete without a stop in its small but charming downtown. Here, you’ll find streets lined with historic buildings, art galleries, boutiques, unique shops, and restaurants.

Some of the more interesting retail establishments in Lenox Village include Design Menagerie, featuring a variety of unique gifts, home decor, and women’s clothing. (26 Housatonic Street)

Across the street, you’ll find The Bookstore & Get Lit Wine Bar, a combination of new and used books paired with wine tasting. (11 Housatonic Street)

If you’re in town for breakfast or lunch be sure to grab a bite to eat at Haven, featuring freshly baked pastries, fantastic salads, and sandwiches. (8 Franklin Street) Shots Cafe is also a cozy spot to pick up a pastry, some coffee, or a quick breakfast or lunch. (27 Housatonic Street)

And Brava is a great casual option for dinner. Here you’ll find tapas, salads, bruschetta, and a variety of pizzas. (65 Church Street)

Visit Pleasant Valley Wildlife Sanctuary

Pleasant Valley Wildlife Sanctuary - one of the things to do in Lenox MA
Photo credit: NewtonCourt / Flickr

One of the best outdoorsy things to do in Lenox MA is to explore the trails and wildlife at Pleasant Valley Wildlife Sanctuary.

Managed by the Massachusetts Audubon Society, this sanctuary provides visitors the opportunity to go birdwatching and hiking. There are more than 1,000 acres in total with trails meandering through wetlands, meadows, and along the slopes of Lenox Mountain.

Admission to the sanctuary is $5 for adults and $3 for seniors and children. (472 West Mountain Road)

Explore the Ventfort Hall Mansion and Gilded Age Museum

The outside of the Ventfort Hall Mansion and Gilded Age Museum - one of the things to do in Lenox MA
Photo credit: Dave Rogge / Flickr

Located in the center of Lenox, Ventfort Hall, the former residence of Sarah Morgan, the sister of J. P. Morgan, is a grand mansion with intricate architecture and lavish interiors.

It was one of the approximately 75 “cottages” built in Lenox during the late 19th century when the village became a popular Gilded Age destination.

Although Ventfort is still a work in progress and not as well preserved or restored as The Mount, for example, it’s still worth a visit. Inside the mansion, visitors can take a self-guided audio tour to learn about the history and stories behind each room. And after the tour, you can also explore the home’s picturesque gardens.

Ventfort Hall is open daily from 10 AM – 4 PM. Tours are $18 with special pricing for healthcare workers, seniors, children, and members. (104 Walker Street)

Pass the time outdoors in Kennedy Park

Fall leaves on the ground in a forest

Another fun outdoor activity in Lenox MA is to spend time in Kennedy Park. This 200-acre park features numerous hiking trails, scenic vistas of the Berkshires, and picnic spots.

You’ll find nearly 15 miles of trails here, many of which were old carriage roads.

The trailhead can be accessed via Main Street, next to Church on the Hill, in Lenox town center. Alternatively, access is available via Rte. 7, from the Arcadian Shop parking lot.

Maps can be purchased at the Arcadian Shop but you can also get a sense of the trails here.

Go on a train ride at the Berkshire Scenic Railway Museum

at train car at the Berkshire Scenic Railway Museum - one of the things to do in Lenox MA
Photo credit: Richard Haddad / Flickr

Train enthusiasts will want to make time in their itinerary for the Berkshire Scenic Railway Museum‘s Lenox Station Museum.

Here, you’ll be able to learn about the history of trains and how they work and explore a 1903 train depot that’s listed on the National Register of Historic Places. There’s also the opportunity to take a short train ride from the depot to the train yard on an antique train.

The museum is open Memorial Day weekend through Labor Day weekend, only on Saturdays from 10 AM to 2 PM. (10 Willow Creek Road)

Attend a performance at Shakespeare & Company

Another artistic thing to do in Lenox MA is to attend a performance at the renowned Shakespeare & Company, dedicated to presenting Shakespearean plays and contemporary works.

Established in 1978, Shakespeare & Company offers multiple performance spaces both inside and out. Outdoor performances are especially popular during the summer months – performed both on the lawn and in the Roman Garden Theatre.

Tickets can be purchased online. (70 Kemble Street)

Pick up some local produce at the Lenox Farmers Market

Produce showcased at a farmer's market

If you happen to be in town on a Friday during the summer and early fall, be sure to visit the Lenox Farmers Market.

Browse and purchase fresh produce, artisanal goods, baked goods, and more from local vendors. You’ll also encounter musical entertainment organized by Berkshire Busk.

The market runs from the end of May through the middle of September. (80 Church Street)

Explore the Frelinghuysen Morris House & Studio

The outside of the Frelinghuysen Morris House and Studio
Photo credit: Vlad b / Creative Commons

Another cultural thing to do in Lenox MA is to explore Frelinghuysen Morris House & Studio, the former home of abstract artists George L.K. Morris and Suzy Frelinghuysen.

Built in the 1940s, this white stucco home was inspired by Parisian artist and Morris’ mentor, Amedee Ozenfant’s private studio and apartment. It also takes inspiration from modern architecture and the indigenous buildings of Arizona and New Mexico.

A visit to the house and the 46-acre estate will allow you to walk through the building with all its original furnishings.

You’ll also have the chance to view the works of Morris and Frelinghuysen and experience their exquisite collection of American and European Cubist Art including pieces by Picasso, Braque, Leger, and Gris.

The house is open from the end of June until Columbus Day. Visit the website for days open and hours as they change over the season. (92 Hawthorne Street)

Relax at the Wyndhurst Manor & Club

The outside of the Wyndhurst resort and golf club
Photo credit: Kerry Flatley

One of the more luxurious places to stay in Lenox is the Wyndhurst Manor & Club. Here, you’ll have the option of booking a room in an 11-room Gilded-Age mansion or a newly renovated Beechers cottage.

This luxury resort also offers a variety of recreational activities, including an 18-hole golf course, indoor and outdoor pools, tennis courts, spa treatments, a fitness center, cross-country skiing in the winter, and dining options.

Visitors can also purchase day passes to experience what the resort has to offer. (55 Lee Road)

Take in a show put on by WAM Theatre

Another cultural thing to do in Lenox MA is to catch a show put on by the WAM Theatre group.

WAM stands for “Where Arts and Activism Meet”. The driving mission of the organization is to create opportunities for women and girls. They accomplish this by donating a portion of their performance proceeds to local and global organizations focused on gender equality.

Theater productions put on by WAM tend to focus on social justice issues, often related to the organization’s mission.

While WAM Theatre is based in Lenox, its shows are performed throughout the Berkshire region. Check the website to see which production is currently being performed and where.

Visit the Lenox Historical Society

If you’re a history buff you’ll want to stop in at the Lenox Historical Society, housed in the 1815 Academy Building.

Explore the exhibits and learn about the history and heritage of Lenox and its residents. Exhibits change throughout the year.

The Lenox Historical Society is open Thursday, Friday, & Saturday from 11 AM to 3 PM or by appointment. (65 Main Street)

Wander through local art galleries

An art gallery in downtown Lenox MA
Photo credit: Kerry Flatley

Not surprisingly the arts community in Lenox also extends into numerous art galleries.

Most galleries are clustered around the downtown, also referred to as Lenox Village. So it’s easy to combine a visit to the village with exploring local art.

Here are a few of the local galleries in Lenox Village:

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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