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Berkshire County wine business changing hands, but staying in the family

  //food-wine.news-articles.net/content/2025/10/20 .. ss-changing-hands-but-staying-in-the-family.html
  Published in Food and Wine on Monday, October 20th 2025 at 23:55 GMT by WNYT NewsChannel 13
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Berkshire County has long been known for its picturesque hills, historic villages, and thriving arts scene, but one of its quiet cornerstones is the family‑run wine shop that has become a staple for locals and tourists alike. In the latest edition of WNYT’s “Upstate of Business,” a detailed profile follows the shop’s journey through a generational hand‑off, highlighting how the business remains rooted in family tradition while embracing new opportunities.

A Legacy in the Hills

The shop, which opened in 1992, was founded by longtime resident Robert “Bob” McDermott, a graduate of the University of Massachusetts with a lifelong love of viticulture. In the opening days, the modest storefront in the center of Lenox carried a handful of locally sourced wines, a handful of national favorites, and a handful of craft beers. “We wanted a place where people could taste the region without having to leave the town,” McDermott recalled in an interview. His mission was simple: provide a curated selection of wines that reflected the quality and character of the Berkshire region while fostering a welcoming community hub.

For over two decades, the shop grew in tandem with the town’s tourism boom. It expanded its inventory to include a robust selection of French and Italian varietals, boutique Californian wines, and a carefully chosen assortment of spirits and artisanal spirits made by local distillers. The shop also began hosting tasting events, educational seminars, and wine pairings with nearby restaurants, cementing its status as a cultural hub.

The Hand‑off

Now, more than 30 years later, the shop is again on the cusp of change. Robert’s son, Thomas McDermott, has taken the helm, but the transition has been more than a simple shift in title. Thomas, who earned a business degree from Yale and spent several years working in the wine trade in Napa, has pledged to keep the shop’s original ethos intact while injecting fresh ideas.

Thomas explains that the decision to step in was driven by both necessity and opportunity. “My father’s health was deteriorating, and I saw that the shop’s future depended on having a steady hand at the wheel,” he said. The McDermott family’s long-standing relationships with suppliers and local producers have ensured that the transition will be seamless.

The shop’s website—updated during the hand‑off—provides a timeline of the business’s history, a list of featured wines, and a calendar of upcoming events. The website’s “About” section notes that Thomas will continue to host monthly tasting nights, but with an emphasis on emerging local wineries and the increasing popularity of natural wines. Additionally, a new online store has been introduced, allowing visitors from the broader region to purchase their favorite bottles and receive them at their doorstep.

Modernizing Without Losing the Heart

While the family’s stewardship remains the cornerstone of the shop, Thomas has outlined several initiatives aimed at modernizing the business. First, the shop has added a “wine of the month” subscription service, giving regular customers a curated selection of five bottles delivered quarterly. This service is designed to tap into the growing demand for experiential wine consumption and to keep the shop’s inventory fresh and dynamic.

Second, the shop will partner with local bed‑and‑breakfast establishments and boutique hotels to offer in‑room tasting kits. The initiative aims to bolster the local tourism economy while increasing the shop’s footprint beyond its physical location.

Finally, Thomas plans to expand the shop’s social media presence. An Instagram account dedicated to “Berkshire County Wine” has already begun to showcase the shop’s weekly specials, behind‑the‑scenes glimpses of the tasting room, and profiles of local winemakers. The shop’s Facebook page, meanwhile, will be used for event announcements and community outreach.

Community Impact

The article also underscores how the shop’s longevity has benefited the surrounding economy. Local vineyard owners report increased sales due to the shop’s commitment to sourcing from nearby growers. According to the shop’s sales records, approximately 55% of its inventory comes from Berkshire‑area producers, fostering a local supply chain that has helped the region remain competitive in the broader New England market.

The shop’s commitment to education is another key benefit. Its tasting events have served as an informal classroom for wine enthusiasts, providing insights into grape varietals, terroir, and winemaking techniques. The shop also hosts a yearly “Wine & Arts” event in collaboration with the local arts council, where attendees can sip wine while viewing exhibits from regional artists.

Looking Ahead

Thomas McDermott’s vision for the future balances respect for the shop’s roots with an ambition to grow. He intends to keep the storefront as a gathering place for locals and visitors, while leveraging digital tools to extend the shop’s reach. “We’re keeping the same mission—connecting people with great wine and good conversation—while adapting to the times,” Thomas said.

For anyone who has walked through the shop’s doors over the past 30 years, the transition feels like a natural progression. The familiar bell over the door, the scent of oak barrels, and the steady hum of conversations about a new vintage remain the same. In a region that values its heritage and is open to innovation, the Berkshire County wine shop stands as a testament to both continuity and change.