What is it like to live in Lenox?

Location, Location, Location
People picnic on the lawn in front of the Koussevitzky Music Shed at Tanglewood.
People picnic on the lawn in front of the Koussevitzky Music Shed at Tanglewood. Hilary Scott for The Boston Globe

Incorporated in 1767 in a region once described as “a hideous, howling wilderness,’’ Lenox was “discovered’’ during the Gilded Age — that is, wealthy New Yorkers decided it was a nice place to spend the summer. A building boom took place, and by 1900, enormous summer “cottages’’ dotted the rolling hills of this Western Massachusetts town.

More than a century later, most Berkshire cottages are either gone or have long since been converted into museums and hotels, nursing homes, and condos. But this town of 5,025 retains the sense of itself as a privileged, distinctive community. Lenox plays host to the Boston Symphony Orchestra each summer at Tanglewood. Only in Lenox do the residents spend years squabbling over whether the new stone belvedere in Kennedy Park ruins the parcel’s scenic vista.

It is easy for neighbors (and some inhabitants) to roll their eyes at Lenox, with its picture-perfect downtown and its high school sports teams called the Millionaires. But the Lenox of 2014 is more complicated and less privileged than the postcards suggest. Restaurants serving $28 entrees have long lines on summer weekends, yet 28 percent of students in the elementary school qualify for free or reduced lunch — about double what the figure was in 2008. That shift is, in part, an indication of how hard the recession hit this tourism-dependent town and the rest of Berkshire County. (Due to the region’s school choice policy, not all of the children who attend Lenox public schools reside in town.)

Still, Lenox — a popular housing choice among the doctors at Berkshire Medical Center in Pittsfield — shows few outward signs of financial distress. Its lawns are manicured. Its houses are covered in historical plaques. Residents may complain about Tanglewood traffic, but they also take deserved pride in being the town that everybody wants to visit —  just as they have since the Gilded Age.



Years a home must have existed in Lenox before it qualifies for “historic house’’ status. Owners of those built before 1923 can get a special plaque to boast of their home’s antiquity.


Annual visitors to Tanglewood, the summer home of the Boston Symphony Orchestra (With just 5,025 residents, that makes for a ratio of visitor to Lenox resident of about 70:1)


Years that the late Senator Edward M. Kennedy spent at boarding school in Lenox. Kennedy attended the Cranwell Preparatory School for his eighth-grade year before transferring to Milton Academy. Like several small boarding schools in the Berkshires, Cranwell swapped education for tourism in the second half of the 20th century. It’s now the site of a four-season resort.




Picturesque, walkable downtown with many fine restaurants, elegant shops, and a nice library


Employment opportunities

Like the rest of the Berkshires, professional jobs are hard to come by in Lenox. Retirees and second-home owners are a significant force in town, sometimes a source of resentment among year-rounders.



In the summer, every night has competing cultural events. Concert at Tanglewood? Performance at Shakespeare & Company? You’ll run out of time before you run out of choices.


Stark months

Winter can feel desolate. When “cottage’’ owner Edith Wharton set her novella “Ethan Frome’’ in the Berkshires, she created the fictional village of “Starkfield’’ — an apt description of the February landscape of Lenox she had experienced.

Edith Wharton’s home known as The Mount. —Matthew Cavanaugh for The Boston Globe
The grounds of Edith Wharton’s home. —Matthew Cavanaugh for The Boston Globe
Ventfort Hall Mansion and Gilded Age Museum. —Matthew Cavanaugh for The Boston Globe
Patrons sip coffee at Shots Cafe on Housatonic street. —Matthew Cavanaugh for The Boston Globe
A view of the Stockbridge Bowl, also known as Lake Mahkeenac, is seen from the lawn at Tanglewood. —Matthew Cavanaugh for The Boston Globe
A pedestrian walks at the corner of Church and Housatonic streets in Lenox. —Matthew Cavanaugh for The Boston Globe

Alison Lobron is a freelance writer in Great Barrington. Send comments to [email protected]