The children of the Catskills generation make a new Jewish home in the Berkshires
A new Chabad house in Lenox is the latest sign of a Jewish metamorphosis in a western Massachusetts vacationland
Rabbi Levi Volovik stands on the back porch of the new Chabad of the Berkshires in Lenox, Massachusetts, which includes views of the Berkshire Hills. Photo by JTA
By Andrew Silow-Carroll August 7, 2025
(JTA) — LENOX, Massachusetts — The new Chabad of the Berkshires here is just down the road from Tanglewood, the summer home of the Boston Symphony Orchestra, and just off the main street (called “Main Street”) where Ethan Frome, the title character in Edith Wharton’s 1911 novella, took an ill-fated sled ride with his wife’s cousin.
“We’re in the Times Square of the Berkshires!” says Rabbi Levi Volovik as he leads a tour of the gleaming, $12 million building, which opened in July. He goes on to list some other attractions that make the Berkshires the Berkshires, at least for the well-off Bostonians and New Yorkers who come in the summers for the arts and the sunshine and the farm-to-table restaurants and the boutiques selling hand-thrown pottery and alpaca cardigans.
“We are a mile from Canyon Ranch, a mile from Miraval, a mile from Shakespeare & Company, and a mile and a half from Kripalu,” he said, ticking off two luxury resorts, a renowned theater company and a yoga retreat center.
What he doesn’t say is that a Chabad center — with its spaces for prayer and celebrations, an Oct. 7 memorial, men’s and women’s ritual baths and guest rooms — may be miles away from a lot of people’s conceptions of a region associated with Norman Rockwell’s sweetly cornball Americana and the hippy epic “Alice’s Restaurant.”
But in recent years, there’s been a Jewish metamorphosis in western Massachusetts, most notably in the summers. Before COVID, vacationing Jews were already flocking to area inns and bed-and-breakfasts. The pandemic led to a boom in second-home buying, drawing professionals from the big cities (Boston and New York City are roughly equidistant from Lenox). The hills are alive with the sound of lawyers, psychologists, rabbis, Jewish communal workers and foundation executives Zooming in to their offices back in the big cities.
Like the Jews who vacationed in the Catskill Mountains in the last century, Jews come to the Berkshires not for Judaism, per se, but for the fresh air and the entertainment — albeit noticeably more highbrow than the standard Borscht Belt fare. Actor Zero Mostel is said to have called the Catskills the “circumcised Berkshires.” For the generation that still remembers the Catskill resorts and bungalow colonies, the Berkshires have become the Borscht Belt with a graduate degree.
Shops sell Judaica alongside the “Life is better at the lake” tchotchkes. Weekly screenings at the summer-long Berkshire Jewish Film Festival draw hundreds of people. The Jewish Theological Seminary and Hebrew Union College each hold summer programs in the Berkshires, combining lectures by faculty and their respective chancellors with fundraising.
At last week’s opening reception for HUC’s annual weekend in the Berkshires, professors and administrators mingled with summering rabbis and local philanthropists — including Harold Grinspoon, founder of the PJ Library program for young Jewish families, whose foundation gives to a number of local institutions, including Chabad.
Conspicuously, the arts institutions that make the area a summer draw have taken notice. The Berkshire Theatre Group, which last month staged Ari’el Staichel’s one-man play about his Yemeni-Israeli background, hosts, with the Jewish Plays Project, a “Festival of New Jewish Plays” in August. Shakespeare & Company will hold “Celebrating Jewish Plays: An Immersive Weekend of Staged Readings” in the fall. “Joan,” a new play about Joan Rivers, is running at the Barrington Stage Company this month. Billy Crystal workshopped his “Mr. Saturday Night” musical at the Barrington Stage Company before taking it to Broadway.
“The Jewish people are among the most substantial donors to all the cultural institutions in the Berkshires,” said Albert Stern, the gabbai, or volunteer sexton, at Chabad and the editor of the Berkshire Jewish Voice, a newspaper affiliated with the Jewish Federation of the Berkshires. “All of [the federation’s] big donors tend to be big donors to places like Tanglewood and Jacob’s Pillow [the summer dance festival] as well. So it’s a natural fit for them to have Jewish programming.”
Dara Kaufman, the executive director of the federation, credits the part-time residents with injecting new energy.
“I think we are blessed here in the Berkshires, both the full-time residents who have invested their time and energy in building this community, and the wonderful second-home owners who are embracing what we are offering and giving back,” said Kaufman, who grew up in Dalton, just east of Pittsfield, the region’s biggest town.
“Growing up here, I think the Jewish community was more insular and still kind of siloed among congregational spaces,” she added. “Now I think we’re much more of a cohesive Jewish community that supports and collaborates with one another.”
Jews have been a year-round presence in the area since the 19th century, when the area hummed with textile mills. (Fun fact: The Berkshire in Berkshire-Hathaway comes from a cotton plant in Adams.) A huge General Electric complex, since shuttered, brought more Jews to Pittsfield, which has two synagogues, Congregation Knesset Israel (Conservative) and Temple Anshe Amunim (Reform).
In Great Barrington, at the southern end of Berkshire County, there’s the egalitarian, lay-led Berkshire Minyan that uses the Conservative prayer book, and Hevreh, a Reform synagogue that celebrated its 50th anniversary in June. To the north is the Reform Congregation Beth Israel in North Adams.
Two figures are often credited with making what was then a WASPy summer redoubt, where hotels and some communities once barred Jews, more welcoming. The better known is Leonard Bernstein, the famed conductor who brought glamour and renown to Tanglewood for 50 seasons starting in the 1940s. Famously, Bernstein declined a suggestion from Tanglewood’s founder, the Jewish-born Serge Koussevitzky, that he change his name if he hoped to flourish in the classical music world.
“Bernstein came up after the war, and he broke it open for the Jews,” said Rabbi Jan Kaufman, a former director of special projects at the Rabbinical Assembly who has decamped from Washington, D.C. to the Berkshires for 25 summers.
Bernstein wasn’t alone. In 1949, a transplanted New Yorker named Bruno Aron left his job at the Pittsfield Jewish Community Center and looked to open a hotel in Lenox that would admit Jews and other minorities. He and his wife Claire bought a dilapidated Gilded Age mansion (now known as Ventfort Hall) and turned it into Festival House, which offered lodgings, art classes, a gallery, a swimming pool and musical and theatrical performances by and for the artists and art lovers who stayed there.
It stayed open until 1961, when, satisfied that the Berkshires had come to tolerate what local authorities had once called “questionable characters,” Aron moved back to New York City with his family and sold Israel Bonds.
The new Chabad house, in some ways an heir to the Arons’ vision, suggests all that’s changed in the years since. But any talk of a Jewish boomlet in the Berkshires comes with a caveat: The surge is seasonal, and the population is aging. Like the audience for classical music, the Jews you run into at Tanglewood or the film festival are mostly retired or thinking about it. The young Jews you do meet tend to be their kids up for a weekend, or dropping their own children off at Camp Eisner in Great Barrington or Crane Lake Camp in West Stockbridge, both affiliated with the Union for Reform Judaism. (Despite its name, Camp Ramah in the Berkshires is actually about an hour’s drive south of the southernmost edge of Berkshire County.)
The region, too, has been losing young people. According to Dara Kaufman, COVID saw a significant decline in the area’s population among people ages 19-34, despite the exodus from the cities. Religious school enrollment and synagogue memberships have suffered, she said.
In a sign of that decline, Anshe Amunim, founded in 1869, is looking to sell its Pittsfield building, and will take space at the neighboring Knesset Israel.
Even before COVID, the federation exec said, “we moved a lot of programming into the broader community. It really was a way to engage people who aren’t engaged at all. And we’ve gained traction.”
Hundreds attend annual Chanukah celebrations at the Mount, the grand mansion in Lenox where Edith Wharton (no great fan of social-climbing Jews) lived from 1902 to 1911, and Hancock Shaker Village, a farm museum. On Aug. 6 Kaufman expected at least 60 people for “Newish and Jewish,” a welcome event for newcomers in Great Barrington. The federation also partners with the local arts venues, demonstrating to them the strength of the audience for Jewish programs.
Sarah Singer, 32, is looking to counter the graying trend. A career and life coach and nonprofit consultant, she grew up in Lenox and Pittsfield. Her family belonged to Knesset Israel, and she went to the area’s sole Jewish day school, Sinai Academy, which opened in 1994 and closed in 2012.
Like many other Jews she grew up with, she gravitated to Boston as a young adult. Unlike many of them, however, she and her husband, who works remotely in tech, returned to the Berkshires in 2024. “We were wanting something different and something more aligned with our values,” she said.
Singer suspects there are perhaps “dozens and dozens” of area Jews in their 20s, 30s and 40s, and, given the cost of housing in the cities and the rise of remote work, more will follow. She has begun organizing events for them through the Jewish federation. Last month, 15 came out for a “Booze & Shmooze” at a local brewery. The mailing list of the unnamed initiative has 75 names.
“The intention is to bring people together, nondenominationally, who might not be serviced or supported by a congregation,” she said. “There’s so much happening here, but it doesn’t quite cater towards people in this demographic. We want to make sure that there’s a space that’s outside of institutions, just to meet people where they’re at, like in their homes, at a brewery, in a sukkah, things like that.”
Chabad takes a similar come-as-you-are approach, only rooted in the Orthodoxy of its emissaries and the philosophy of the late Lubavitcher rebbe, Menachem Mendel Schneerson, who believed that every ritual act performed by a Jew, any Jew, brings the world closer to redemption. Sixty to 80 people will attend Shabbat morning services in Lenox during the summer, but Volovik says ”99%” of those attending the Chabad ribbon-cutting weren’t Orthodox.
“I don’t believe in Orthodox. I don’t believe in Conservative. I don’t believe in Reform. OK? I believe in tradition,” said Volovik.
Like most Chabad emissaries, Volovik and his wife and partner, Sara, don’t depend on year-round members paying dues, but rather enthusiastic donors who are happy to support an institution that functions as much like a Jewish community center as a synagogue. A program guide lists lectures by Middle East experts, a challah bake, mah-jongg Mondays and film screenings.
Born in Crown Heights, Brooklyn, Volovik, 50, staffed Chabad outposts in Romania and Bulgaria before opening a Chabad in Pittsfield in 2003. In 2018 he bought a mansion in Lenox, built in 1863, that he hoped to renovate, but which he described as a money pit. When he decided to raze the building, Volovik got pushback from some community members and the local historical society (which he calls the “hysterical” society), but prevailed under a state law that “spares religious or educational institutions from many zoning requirements,” according to the Berkshire Eagle. The new building looks like a suburban “professional” building with a few Yankee grace notes.
Seven hundred people attended the opening of the new Chabad on July 6, including local politicians. The classical pianist Emanuel Ax, a fixture at Tanglewood, performed.
The Voloviks have plans for a day camp and a religious school on the site. There’s a music room, a playground, a basketball hoop and a pickleball court. Having provided takeaway kosher food during the pandemic, Volovik plans to open a kosher steakhouse, perhaps by next summer.
Volovik is aware that such a conspicuous Jewish presence in Lenox might have been unthinkable in an earlier era, and says that if one sort of antisemitism has faded, others have taken its place: One of his sons is doing outreach at Williams College in the northern Berkshires, where some Jewish students felt intimidated by a pro-Palestinian encampment that went up in 2024.
He also acknowledges that even some Jews might be wary of such a big Jewish footprint in a quaint New England town.
“There was a time that Jewish people once were desperate to fit in. They wanted to be part of the melting pot. But I think now, America has grown very, very more mature than they had been then,” he said. “People respect diversity, and it’s okay: You don’t have to be me and I don’t have to be you. I could be who I am.”
