5 things to do when visiting Lenox

Do yourself a favor and explore the green spaces when visiting Lenox, a town expert says.

Mass Audubon’s Pleasant Valley Wildlife Sanctuary in Lenox. Mass Audubon

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Lenox boasts historic mansions and museums, top-ranked resorts, and locally sourced restaurants, as well as the world-famous music venue Tanglewood.

But what visitors may not know about the well-known Berkshires town is how fabulous its parks are, said Kerry Sullivan, town clerk for five years and a Lenox employee for 28 years.

“The parks, in general, are a hidden gem, the parks all over town,” she said.

Ahead, discover some of Sullivan’s picks for where to go and what to do in Lenox.

Plan a nature escape.

A Lenox park loved by locals — and Sullivan’s personal favorite — is the 500-acre Kennedy Park, which offers old carriage roads and nearly 15 miles of groomed trails. Visitors can hike, cross-country ski, snowshoe, and mountain bike in the park. Tripadvisor reviewers have called the park “beautiful and peaceful and serene” and a “fantastic place to escape civilization.” Here’s a map.


Sullivan also loves spending time at smaller area parks such as Lilac Park, a charming 1 ½-acres in the Lenox Historic District filled with lilacs and benches and where community events such as summer concerts and craft fairs are typically held. The Lenox Garden Club restored the 1908 park in the 1990s, planting 100 lilacs, 10 Canadian hemlocks, small shrubs, and 1,500 daylilies. The 5 ¼-acre Tillotson Park is also a favorite of Sullivan’s because there is a baseball field named after her father-in-law, Bob Sullivan, a local baseball star.

Mass Audubon’s Pleasant Valley Wildlife Sanctuary is always a treat, Sullivan said, with its 1,300 acres of forests, meadows, and wetlands, along with seven miles of well-marked trails. Among outdoor activities enjoyed at the sanctuary are birding, canoeing, snowshoeing, and hiking. Hikers can choose from beginner trails to more challenging hikes to the summit of Lenox Mountain at 2,126 feet.

“We’re so fortunate,” she said. “It’s all right here.”

Explore a historic mansion.

One of Sullivan’s favorite places to experience culture in Lenox is The Mount, Edith Wharton’s Home, a 1902 Gilded Age mansion and the former home of the Pulitzer Prize-winning author. The property, a National Historic Landmark, welcomes more than 50,000 visitors annually.

“Who doesn’t love historic homes?” Sullivan said.

Visitors can walk the halls of the 35-room white stucco mansion and peer into the rooms where the author once lived, check out her library, take in historic photos and artifacts, stroll the gardens, and view re-imagined rooms used by former workers, such as the kitchen and sewing room. This summer, guests will encounter large-scale contemporary sculptures throughout the property, thanks to a collaboration with SculptureNow.


Sullivan also loves the mansion’s year-round artistic and literary programs, whether it’s live music on summer nights or a virtual book club featuring author talks over Zoom.

Eat like a local.

When all of that exploring makes you hungry, do yourself a favor and grab a bite to eat at River Dale Market and Deli, Sullivan said, where the sandwiches are fantastic; she loves the veggie hummus wrap, made with homemade hummus. Customers can build their own sandwiches, choosing from various meats, cheeses, breads, and toppings, or order homemade pasta, chicken, and tuna salads.

Sullivan said she’s most likely to meet a friend at The Olde Heritage Tavern in downtown Lenox, which offers inside and outside dining. The restaurant is known for its burgers and also serves wings, soups, sandwiches, and wraps.

“The Heritage is where you go to meet people,” she said. “You’ll see the people that make Lenox so special. It’s where locals gather.”

kayaker in lenox, ma

A kayaker explores Woods Pond in Lenox.

Consider the time of year you’d like to visit.

When planning a trip to Lenox, consider the time of year that suits you, Sullivan said.

“In the summer, it’s really busy,” she said, noting that Tanglewood concerts and other cultural activities are usually in full swing.


Tanglewood, the summer home of the Boston Symphony Orchestra, canceled its 2020 live season due to the coronavirus pandemic, but will offer a shortened concert season this summer from July 9 to August 16 with about 50 percent of its usual seasonal offerings.

In the fall, folks come to town for leaf peeping, fall festivals, and the Josh Billings Triathlon, Sullivan said. The latter is billed as one of the oldest and largest bike-canoe-run triathlons in the country and raises money for the Berkshire United Way. Josh Billings is the pen name of 19th century humorist and Berkshires native Henry Wheeler Shaw.

“Fall has gotten to be very busy,” she said. “And we’re a destination place for weddings, too.”

Winter and spring are the quieter seasons, Sullivan said. However, there’s still plenty for Lenox visitors to see and do, from museum excursions to dining out to biking, hiking, cross-country skiing, and snowshoeing.

“It’s a wonderful community,” Sullivan said. “I think it really has it all. And the people will welcome you.”

What readers say about Lenox:

When we asked readers to share what they love about Lenox and the best activities in the area, one response was quite popular.

Michele Hurt answered simply: “Tanglewood.”

“Tanglewood,” wrote Marla Murphy Smith, then added: “Breakfast at The Haven, pizza at Betty’s Pizza Shack, and then a quick drive to Pittsfield for what ever is on tap at Wandering Star Craft Brewery.”

“Tanglewood definitely,” wrote Pia Margareta Kyto. “Many nice memories during several years.”


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