Worcester Business Journal

wbjournal.com | February 23, 2026 | Worcester Business Journal 21 HALL OF FAME F O C U S BY ERIC CASEY WBJ Managing Editor R alph Crowley Sr. wanted his children to be hockey players. e only problem? ey couldn't skate. "We were flops," said Jeff Crowley, co-owner, president and CEO of Wachu- sett Mountain Ski Area. "We had bad ankles. Who knows what it was, but we couldn't skate for beans." Seeking an alternative winter activity for his five young children, their dad tried a ski trip to Mount Snow in Vermont instead. e Crowley kids took well to the slopes, draining their dad's wallet in the process. "He ended up spending over $100 on a Saturday," Jeff Crowley said. "Anyone that can get $100 out of Ralph Crowley has got to be doing something right." e financial hit he took on that ski trip le a lasting impression, and in 1969, Crowley Sr. and his business partner decided to bid on the lease for the ski area at Wachusett Mountain, then a modest, state-run slope. eir $16,002-bid was successful, and today, Wa- chusett Mountain Ski Area is the crown jewel of the growing Central Massachusetts tourism scene. Bringing in about 1 million visitors per year and employing around 1,500 at peak season, Wachusett is the most popular ski area in southern New England. e 2,006-foot mountain is a top destination for skiers and snowboarders of all ages, from high school ski clubs to silver-haired athletes in their 90s. "We have old-time skiers in the morning," Carolyn Stimpson said. "ey can barely walk, but they still can ski, because of gravity. And then around 3 o'clock, the school kids – we call them Liquid Plumber – they all come flying in. And then the nightly corporate racers come, and they're all coming in to race down the course, so they can go drink a beer." Stimpson, the only daughter of the family patriarch, serves as Wachusett's co-owner and vice president of resort services and is a familiar face from the business' inescapable television commercials. She's clearly proud of the whole operation, but something that sticks with her is the business' net promoter score, a metric mea- suring customer satisfaction and loyalty. "We have a comp set of very similar-sized ski areas, and our likelihood to recommend and likelihood to visit is 19 points over that set," Stimpson said. "We really appreciate that people are loyal to us." A throughline between Wachusett Mountain and the Crowley family's other major business venture, Worcester drink manufacturer Polar Beverages, is the ability to compete with much larger corporate players. Even as other smaller ski venues across the state have closed, Wachusett has remained strong, com- peting with larger companies in the space, said Roy Nascimento, president and CEO of the North Central Massachusetts Chamber of Commerce. "ey have been able to compete very, very well against the big ski resort players out there, these mas- sive corporations," he said. "ey really embody that community spirit and family business culture." Significant improvements, including the installa- tion of a new high-speed chairli as the latest part of $20-million worth of upgrades, has helped keep the ski resort in modern times. Jeff and Carolyn have persisted, even aer the tragic loss of their brother and mountain mainstay David Crowley, who passed away in 2024 aer a battle with a rare brain disease. Wachusett regularly punches above its weight, having been named the eighth-best ski school in the country by USA Today in 2025. Ski Magazine named it the 15th best ski resort in the eastern part of the country the same year, toppling mountains double its size. e profile noted the consistent presence of own- ership, the resort's affordability, and well-kept slopes. In the age of online marketing, the importance of the business' famous "Wa–Wa-Wachusett" commercial jingle, once inescapable of local television, has taken a back seat to targeted digital advertising campaigns, but the song continues to be an earworm, Stimpson said. e jingle was based on a song called "e Wah-Watusi," a minor 1960s dance hit performed by R&B group e Orlons. "We were in Australia skiing, and all of a sudden, somebody behind me was singing it, because I had a sticker on my helmet," Stimpson said. e catchy tune isn't the only thing that sticks, Jeff said, recalling a conversation with a skier. "e customer said 'I just have to tell you that I've been to a lot of different businesses over my years, and I just really have to remark on the quality of the culture that you have,'" Jeff said. "at starts with us two, but we try to develop good work habits with these young folks, but also make it fun." PHOTO | MATT WRIGHT Crowley & Stimpson bring millions to Wa–Wa-Wachusett WBJ Hall of Fame Jeff Crowley & Carolyn Stimpson Co-owners President & CEO (Crowley) Vice president of resort services (Stimpson) Wachusett Mountain Ski Area, in Princeton Employees: 1,400-1,500 Annual attendance: ~1,000,000 W Carolyn Stimpson (center) and Jeff Crowley (far right) with the next generation of Crowley leadership at Wachusett Mountain (from left): Director of Operations David Crowley Jr., Public Relations Manager Chris Stimpson, and Ski School Director Courtney Crowley

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