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This Massachusetts Ski Area is Winning the Fight to Stay Independent

Wachusett's Crowley Clan is several generations deep into ski-area ownership and can say one thing for sure: It's not the size of the slopes or the vertical feet that matter—it's the amount of heart that goes into a mountain that makes it special.

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This article—and many more like it—is available exclusively to Active Pass members, along with a host of others benefits such as access to the Warren Miller Entertainment film archive (that’s 50-some films), ski-instruction and fitness video tutorials, pro deals and members-only industry discounts, and a print subscription to SKI. Learn more about Active Pass or join here.


The sun is barely peeking over the rolling hills of Princeton, Mass., and already, Wachusett Mountain is vibrantly alive.

In one nook of the cavernous base lodge, the home-school parents set up shop, prepping for another day of teaching their kids by way of the mountain. Nearby, a women’s ski program congregates around a coffee station, amped about the demos available slopeside that day. In nearby schools, little minds try to focus on math or history but can only count the minutes until the bus takes them to Wachusett for their late-day ski and ride programs. In offices in greater Boston, working adults think about their gear in the car and how good it will feel to night-ski and après later.

And in the parking lot, lifetime Wachusett skier Richard Granger pulls in with his left boot already on (easier to get to the lift quicker), yanks on his right, grabs his skis and dashes to the lift to meet up with the “10x10s”—a gang of adult skiers who aim for 10 runs by 10 a.m. daily. Swathed in the early-winter morning sun, Granger feels blessed every time he arrives. He, like them all, is at home.

Wachusett Mountain, located far enough from Boston to feel away from it all but close enough to see the skyline from a trail, could be seen as a microcosm of the world and those who thrive in it. But it’s more than that. With its a-place-for-truly-everyone vibe, seamless accessibility, and almost magical ability to feel so big when it’s a “day hill,” Wachusett stands as proof positive that, done right, mountain sports life truly can be for everyone. It may not be hyperbole to say Wachusett represents what our world can be: inclusive, cooperative, and happy.

Funny thing: Had the children of Wachusett’s owner—the late Ralph Crowley—taken to hockey, the ski area might not exist.

“My dad was a hockey guy, but none of his kids could skate,” Carolyn Crowley Stimpson, the only daughter of his five children, says. The kids begged their dad to let them try skiing, so he loaded them in their green station wagon and headed to Vermont’s Mount Snow for the day. The kids took to skiing and Dad, a savvy businessman who had grown Polar Beverages to huge success, had a light bulb moment as he paid for his kids to head out and then watched the ticket window line.

“Six bucks each for lift tickets; more money out of his pocket in the rental shop,” she remembers. “We couldn’t take the Pike home because he had no money left for tolls.”

So when the state put then tiny Wachusett Mountain up for lease, he saw opportunity. “He said, ‘anyone who can make Ralph Crowley empty his pockets of money on a Saturday has a great business,’” she laughs.

And so, the Crowley family took over Wachusett in 1969 with a bid for a five-year lease at $16,002. His then 10-year old son, David, suggested that amount. That wasn’t just a lark: Crowley, from the start, used his family as his divining rod for what the mountain needed. To this day, the Crowley family is on site and hands on, not just running the place, but also enjoying it. Since they are a family of individuals united by their love of the mountain and the sport, they may just be the key to Wachusett’s continued success.

In-action views of Lake Wachusett. Photo: Courtesy of Wachusett/Rob Bossi

Some 2019 season numbers for your perusal: 30,229 ski or snowboard lessons. 19,514 NASTAR runs (making them the number one in the country). 36,353 French fry baskets sold. 32,003 signature cider doughnuts (made on site) sold. 117,000,000 gallons of water pumped through to maintain a raved-about surface all season long.

Sounds like a lot, given that Wachusett is really just one (very large and well planned) base lodge, three quads, one triple, and four magic carpets servicing 29 trails on a 1,000-foot vertical drop. And yet, the flow of the resort and the stoke of the skiers and riders make it work.

Related: These Resorts Have Risen in the SKI Mag Rankings For The Last 5 Years—Can They Keep it Up?

As does the family. Any given day you’ll find Carolyn slinging chicken nuggets, helping in the rental shop, mingling in the base lodge, and of course, skiing the trails. (She skis the runs named for her parents, Frannie’s Folly and Ralph’s Run, in their memory every day she is here.) She and her brother Jeff star in the area’s weekly ubiquitous commercials (If you live in New England, even if you don’t ski, you say “Waa-waa-Wachusett,” when you name it), and the next generation of Crowley young adults is stepping up as well, joining the family business in that same in-public and hands-on way.

Skier in air with crossed skis
Kevin Sweeney crosses it up in Hitchcock, one of two terrain parks at Wachusett. Photo: Courtesy of Wachusett/Andrew Santoro

It’s impossible, in other words, to separate that multi-generational owner family from the mountain itself. They are one and the same. And it works. “They’re part of the whole vibe there,” Granger says of the Crowleys. “You walk in and go past the first timers in the ticket line (and think: who buys tickets at window prices?) and one of them is there helping. Then you go past the ski shop and you see Carolyn in there helping move things along. You go past the coffee shop where the race teams folks hang out nearby and one of the Crowley kids is asking about their results.”

Up in the Coppertop one of Wachusett’s restaurants that happens to pull a perfect Guinness, is where all the townies hang out, says Granger. “The older folks, you know, the 75-and-up group, are drinking coffee there,” he laughs. “They are not as eager to get right out anymore. And in the middle of it all, you see Jeff Crowley shooting the breeze with them all. It’s really great.”

All those scenes transition as the day shifts to afternoon: School groups take over, and then the sun sets behind those hills again, making way for the after-work skiers, the night-ski league racers, and always the après lovers.

How do they all keep moving and feel spread out on the hill? Chalk that up to top-notch lifts (the central lift zips you to the top in four minutes), well-designed trails (a fight for which almost shuttered the ski area in the 1990s), and that Crowley-based dedication to first-person service. The Crowleys work hard to create an atmosphere they’d expect for themselves.

See something not right? They share as a family and make it work, from the simple to the sublime. When third-generation Courtney Crowley was a small child with her staff badge reading “Litter Patrol,” she asked her parents why they sold French fries and grilled cheese in separate baskets (“Who doesn’t want French fries with their grilled cheese?” she asked rhetorically, as only a child can). Now they’re served combined.

When third-generation Chris Crowley developed a penchant for flipping upside-down in the terrain park, the signs that read “No Inverted Jumps” came down and lessons and programs for freestyle were introduced. As they evolve, Wachusett evolves.

Funny thing: Had the children of Wachusett's owner—the late Ralph Crowley—taken to hockey, the ski area might not exist.

Expansive views of Lake Wachusett off of Upper Conifer Connection. Photo: Courtesy of Wachusett/Rob Bossi

Lifts spin at Wachusett starting at 7:30 a.m. and the true loyalists say that’s the time to get out and crank your vertical. But on weekdays, with the fast lifts and spread-out trail layout, it’s easy to get plenty of vert under your edges (this writer has been known to bag almost 20,000 before lunch).

Splitting up your squad for different needs is a snap: trails all empty out to a spacious single base area. And while it’s a day mountain, it offers a cool add-on: Day suites are like slopeside condos without the bedrooms, a nice way to make a day and/or evening there special.

Mornings mean the 10×10’ers crew is racking up the vert, sharing the slopes with the adult racing groups and the home-schoolers. On a powder day, they make room for all the other folks who have been saving mental health days for just that.

By noon things are cranking, and while the multiple food spots are serving great meals, lunch is a good time to keep on taking runs. To tide you over, glide into the Bullock Lodge Cider House, tucked into the trees mid-mountain and home to one of skiing’s greatest on-mountain treats. Built in the 1930s by the Civilian Conservation Corps, it’s now operated by nearby Red Apple Farms and churns out fresh cider doughnuts and steaming hot cider. It should be illegal to not stop in. So good you have to have two? Burn it off with a NASTAR run.

The crowd shifts in the afternoon to the after-school-program kids and high school race teams and then, as evening falls, the night skiers, beer leaguers, and after-work lappers take over. Live music, DJs, and special events are always happening (though the pandemic has slowed that scene down). The lifts spin until 10 p.m., some nights until midnight.

Through the transitions all day and night, one thing remains constant: satisfaction across a wide berth of folks.

Read about Wachusett’s Rank in the Annual Reader Resort Survey.

two women enjoying a meal
The T-Bar serves wine and tapas in a relaxed setting inside the Coppertop Lounge. Photo: Courtesy of Wachusett/Rob Bossi

Terry Harte has skied Wachusett since he was a small child. He’s 64 now, and after raising kids on skis here (he also met his wife here), he’s now a proud member of the 10x10s and will tell you one thing is for sure: It’s always fun to ski Wachusett.

“Smith Walton (one of the resort’s newest trails, although it’s nearing 40 years old) is great,” he says. “The upper part is perfect cruising.” Plus, it’s “never really cold” but almost always cold enough for the snowmaking to pump out great surfaces.

The other trails are entertaining too, like lap-worthy Conifer Connection, or windy Roper’s Road, from which you can spot the Boston skyline, and long and speedy Ralph’s Run, named for the man himself. Bonus: They groom the entire mountain twice a day, so there’s rarely any skied-off trails.

That’s kept Harte happy for a lifelong ski career so far, but like everyone, when asked what makes it stick, he points to the Crowleys.

“The people who run it are great,” says Harte. “Anyone who works here is just so approachable, but you don’t even need to approach them. They approach you.”

Jeff Crowley knows that’s part of the secret to their success.

“It’s almost in our DNA,” he explains. “My dad was the businessman and my mom was the hostess, party thrower, and a great cook. We’re all like a morph of those things. This is like we are just hosting 4,000 of our friends for a ski day. Every day.

“Look, I think Alterra and Vail Resorts are great,” he smiles. “But what smaller gives you is great, too. If you want to talk to us—the owners—or yell at us, you can come right up to us and do it. They say you can’t be all things to all people, but I think we actually are.”

As the next generation begins to take over, they realize the responsibility.

While they once called Wachusett the “Great White Babysitter,” the next generation is stepping up, fully aware of the responsibility. How can you not be when family legend says Carolyn left work at the ski area in full labor, but stopped to fix up some things on the way?

'If you want to talk to us—the owners—or yell at us, you can come right up to us and do it.'

“I hope people appreciate that this family is out there to make this place great,” says Courtney. “We have some really big shoes to fill and we’re going to try our best. They worked so hard to make this what it is, and that makes this a huge responsibility for us. But you know, we’ve seen how change can happen the right way. I mean, look at the grilled cheese/French fry basket,” she laughs. “If it needs to be done, it can be done. Our guests deserve that into the future as well.”

This article was originally published in the January/February 2021 issue of SKI Magazine with the headline “Family Ties.”

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This article—and many more like it—is available exclusively to Active Pass members, along with a host of others benefits such as access to the Warren Miller Entertainment film archive (that’s 50-some films), ski-instruction and fitness video tutorials, pro deals and members-only industry discounts, and a print subscription to SKI. Learn more about Active Pass or join here.