Is Saddleback’s Future Finally Bright?

Big terrain, deep snow, and frigid air at Saddleback Mountain make the resort one of New England skidom’s undisputed greats. But that wasn’t enough to keep it from closing five years ago. Now, Saddleback is back, with a fresh drop of investment — and some lofty ideas.

By Will Grunewald
Photographed by Jamie Walter

In its 56-year history, Saddleback had teetered on the brink of closure a few times, but in the winter of early 2016, the realization that it had really shut down was only just setting in around Rangeley. The ski resort’s owners — retired University of Maine geology professor Bill Berry, his wife, Irene, and their seven adult children — had put the struggling property on the market several years earlier. Some Saddleback diehards had formed a nonprofit foundation to try and purchase the mountain, but that effort petered out. By the summer of 2015, the Berry family had decided that if they couldn’t secure $3 million in outside funding to replace the rickety chairlift that served as the main uphill artery, they wouldn’t open for the following season.

Through late fall and early winter, rumblings of a potential buyer buoyed hopes around Rangeley. The small, outdoorsy western Maine town of about 1,200 year-round residents counted on Saddleback to supply a few hundred seasonal jobs and bring visitors to shops, restaurants, and inns. Eventually, though, it was clear that the mountain had missed the window to open that winter, and public updates from the Berry family became increasingly rare. The following summer, a local group started fundraising to purchase the resort and run it on a co-op model, like Vermont’s Mad River Glen, but the money never came together. 

Meanwhile, Jim Quimby was one of a few employees the Berry family paid to stay and keep Saddleback looking serviceable — mowing in summer, plowing in winter, keeping tabs on the lodge and condos. His mother and his father and his father’s father had all worked on the mountain. With its 4,121-foot summit and 2,000 vertical feet of skiing, it was, by those two measures, only rivaled by Sugarloaf and Sunday River in Maine. 

“I grew up on this mountain,” Quimby says. “This is my place. To come to work every day up here was heartbreaking. To know the potential, to know how great the skiing and the people were here and all the fun we had, it was a real kick in the guts. But I held out because I just couldn’t see it going away.”

A few of the joyful first skiers to visit Saddleback this season.

In 2017, Quimby and the rest of Rangeley saw a light at the end of the tunnel when the Berry family agreed to terms with an Australian holding company called the Majella Group. But the family failed to notice some red flags. The company had a sketchy track record in Australia — stalled projects, a $30 million government contract for flood-relief services never rendered, and a CEO, Sebastian Monsour, who, among other things, had abandoned a run for political office after being exposed for fabricating a rugby career. “Seb is one of those guys who when you’re in a bloody hole he keeps digging,” one politico told an Australian newspaper in 2012. “He’s part Walter Mitty, part big noter, part troublemaker.”

Another winter had passed without skiing when, in early 2018, a recording captured Monsour telling Majella staffers the he “won’t lose any sleep” if Saddleback never opens. Then, that June, Monsour was arrested in Australia for allegedly misallocating $5 million from a Chinese investor. After that, Rangeley residents grew wary of any good news from Saddleback. “I’m a social guy, and I know everybody in this town,” Quimby says. “Each time it seemed like something was happening, I’d get excited and get everybody’s hopes up, and then it would fall apart. I did it so much, people didn’t really believe me anymore. I was the one who cried wolf.”

In the wake of the debacle with Majella, though, a new frontrunner emerged, the Boston-based Arctaris Impact Fund, a deep-pocketed firm that mixes private equity with government and philanthropic support to invest in low-income areas. An official at Maine’s Department of Economic and Community Development, who had worked with Arctaris in the past, suggested to fund cofounder Jonathan Tower that the Saddleback project might be a good fit. Still, discussions between the Berry family and Arctaris were touch-and-go from the beginning and at one point ground to a halt, after then-governor Paul LePage decided against designating the Rangeley area a federal Opportunity Zone, a status that encourages investment in economically distressed communities by offering tax incentives.“ You often see deals that die nine times before they get done,” Tower says, “but this one died 99 times.”

Working behind the scenes to keep the two sides talking were Tom Federle, a Portland lawyer and Saddleback condo owner, and Andy Shepard, a former L.L.Bean exec who had revived a pair of small-town Maine ski mountains as head of the Maine Winter Sports Center (now the Millinocket-based Outdoor Sport Institute). Shepard helped sell the Berry family on Arctaris’s vision. “Getting the mountain up and profitable really is a means to an end,” he says. “The end is that we find a way to leverage that success to make a difference in the community.”

Saddleback general manager Andy Shepard
Saddleback general manager Andy Shepard

Becoming profitable would mean renovating the lodge, adding a new high-speed lift, and putting up a hotel, among other things. Making a difference in the community would start with bringing winter jobs back to the mountain, but it would also involve making more of those jobs into year-round positions — by expanding four-seasons offerings such as white-water kayaking, flat-water paddling, mountain biking, and photography workshops — plus building employee housing and finding ways to provide seasonal workers with year-round health benefits.

Arctaris’s negotiations with the Berry family became protracted and sometimes tense, with terms often shifting and both sides questioning the other’s commitment, but in January of last year, the $6.5 million deal was finally signed, and Saddleback was on track to open again in fewer than 12 months. Then, COVID hit.

Big ambitions alternating with big problems — that’s how it’s always gone at Saddleback. In the 1950s, a few local businessmen noticed the growing popularity of a novel pastime, downhill skiing, and they banded together to open Saddleback in 1960, on New Year’s Eve. They imagined it becoming the “Sun Valley of the East,” but in those early years, two T-bars serviced only a handful of slopes. In 1964, Saddleback jumped to the fore of Maine skiing with the construction of a chairlift that traveled 4,600 feet. It was the longest chairlift in Maine — although there was only one other. Then, the expense of the lift combined with consecutive bad winters to force an ownership change, the first of many. It was around that time that Jim Quimby started skiing every weekend. “We had this little group of local heathen kids, and some of the winter kids from away skied with us, and people called us the rat pack. We just skied in a big kind of gang and razzed everybody. Saddleback people hung really tight with each other.”

Until then, Saddleback and Sugarloaf were more or less considered equals, Maine’s two big ski mountains. But in the 1970s and ’80s, the ski industry went through a period of rapid growth nationally. Some ski areas capitalized, and others didn’t. John Christie, a former manager of Sugarloaf, bought Saddleback in 1972 in hopes of growing the resort. To that end, he added Saddleback’s first 20 condos and planned for much more work on the mountain. Almost immediately, though, the 1973 oil crisis and a run of bad winters derailed his plans, and he sold the mountain in 1975. Meanwhile, Sugarloaf’s ownership managed to pour money into condos and new lifts. Later, it would add a golf course. “There is just some missing link here,” Saddleback manager Dick Frost told Boston Globe outdoors columnist Tony Chamberlain in 1981. “It’s always been like that, just some ingredient we never found.” 

Before a T-bar to the summit was added in 1979, Saddleback topped out a few hundred feet lower than it does today — and a lift has since replaced the dauntingly steep T-bar ride.

One of Saddleback’s most eloquent advocates, Chamberlain covered New England’s ski scene for the Globe for the better part of four decades, starting in the 1970s. While a student at UMaine Orono in the ’60s, he had learned to ski at Saddleback and Sugarloaf, and he always wrote about the former with particular gusto. In one dispatch, on a day when thermometers registered 20 degrees below zero, he observed that the mountain gets “so cold it shines.” 

Chamberlain sometimes seemed near exasperation trying to convey to readers, who were likely headed instead to Vermont or New Hampshire, the grandness of Saddleback’s view out over the Rangeley lakes and its alluring mix of dramatic steeps and classically windy New England–style trails. “I repeat for perhaps the 10th time in print that it is one of the truly great New England ski areas,” he wrote in 1982. “Saddleback manages to pull together the big-terrain skiing experience with the intimacy of a smaller, centrally organized family ski area. I’ve never seen these two elements mixed so well.” 

The big mountain’s small-mountain vibe increasingly came to define Saddleback against Sugarloaf and the then-up-and-coming Sunday River, which was making big investments in snowmaking, grooming, and lodging. But Saddleback — almost three hours from Portland and more than four hours from Boston — was too far afield for most day-trippers, and neither the mountain nor the town could offer many beds. The relative lack of development made it both special and susceptible to failure.

The base lodge received a thorough renovation last year, but COVID-19 is limiting access to indoor space this ski season.

Saddleback’s fading stature wasn’t lost on Donald Breen, owner of a Massachusetts pharmaceutical company, who took over the resort in 1978. Echoing past owners, he talked of turning the area into a “Vail of the East.” The ski business, he realized, had become a real-estate business — by 1987, Sunday River had 568 condos, and Sugarloaf had 730. The next year, Breen announced a $37 million expansion, with plans for adding several hundred condos to Saddleback’s mere 45. 

Such a big development would mean other big changes, longtime Saddleback skiers worried. They didn’t have to look far for an example. “Sugarloaf has 13 lounges and/or restaurants at the base, plus as many more in the valley and nearby Kingfield, Stratton, and Eustis,” a Washington Post reporter wrote in 1988. “In many of the nightspots, a jacket and silk turtleneck (or comparable dress for women) would not be out of place (although a tie might attract attention).” The reporter contrasted this to days gone by, when “wardrobes . . . ran to dungarees, heavy wool sweaters and thick parkas.”

For better or worse, Breen’s plans came to nothing. He believed that the key to marketing Saddleback as a ski destination and a condo haven lay in cutting new runs on the opposite side of the mountain, across the ridge that the Appalachian Trail follows. Lifts would end right alongside the hiking trail, and throughways for skiers would have to be cut crosswise. Conservation groups and the National Park Service balked, blocking the permitting process. Despite having thousands of acres available for development on the side of the mountain where trails already existed, Breen kept up the fight, pouring money into fruitless legal maneuvering instead of into the resort. In 1997, he put Saddleback on the market.

In 1998, Jim Quimby returned from two decades in the Air Force to find Saddleback in bad shape. “It was really at a low,” he says. “Hardly anyone was skiing up here. The owner kind of ran it into the ground.” Chamberlain, the Globe columnist, didn’t wholly mind the situation, writing, “It now remains what it always has been: a rawboned area with an old chairlift, a sparse crowd of skiers, and fabulous skiing.” 

The new high-speed quad chairlift replaced an old snail’s-pace double. 
Jim Quimby manages mountain ops with Emerson, and his grandfather helped build Saddleback’s first T-bars and chairlift in the 1960s.

But restaurant, shop, and inn owners in Rangeley felt the impact acutely as winter business dwindled. Meanwhile, Breen cut a deal with the Park Service that had him surrender 1,150 acres along the Appalachian Trail in exchange for $4 million. In 2003, he announced his intention to close Saddleback. That’s when Bill Berry tapped into his family’s inherited fortune to buy the resort for $8 million. Over time, the Berry family improved snowmaking capacity, doubled the size of the lodge, and replaced the excruciatingly steep T-bar to the summit with a lift. “All of a sudden you started seeing skis on top of cars in front of restaurants and at the IGA grocery store,” Quimby recalls. “It was good for Rangeley.”

Then, just like before, things fell apart. This time, it was the 2007 financial crisis and housing-market collapse, which arrived right in the middle of condo expansion. There were other problems too. Bill Berry loved Saddleback as it was and vowed never to put in high-speed lifts, an amenity that skiers prefer and an asset that increases a mountain’s rider capacity. He thought such lifts were contrary to Saddleback’s low-key atmosphere. Even after the economy recovered from the Great Recession, the resort operated at a loss year after year. Progress came to a full stop, and this time, the lifts did too.

Jared Emerson, who now manages Saddleback operations along with Jim Quimby, grew up skiing Saddleback in the ’80s and ’90s. His grandfather and father were both on the ski patrol, and when Emerson and his sisters were young, the family would drive up from Topsham on weekends, park their pickup out back of the lodge, and plug their camper into the ski-patrol hut for power. “That’s the way we ski-bummed it growing up,” he says. “Fond memories of some cold and windy nights in that camper.”

Emerson joined the ski patrol after he turned 16, then moved to Rangeley after graduating from high school. He worked at Saddleback until the Berry family closed it, in 2015, and then for a few more years doing basic upkeep with Quimby. By the time negotiations with Arctaris were happening, he’d taken another job, running the service department of a snowmobile and ATV shop in town. That’s where he was when a deal was finally signed. 

“I got a text message from Andy Shepard that Saddleback had sold and literally didn’t say a word to the guys in the garage — I just walked out. I don’t even know if they knew I had gone anywhere for a while.” He called his father and grandfather to give them the news, then drove to the lodge where his wife works to tell her in person. “By the time I got there, she already had a shot of tequila on the bar ready to go, because news travels that fast in Rangeley,” he recalls. “The town was just one big party that night.”

third-generation Saddleback skier Jared Emerson has worked at the resort since he was a teenager
Third-generation Saddleback skier Jared Emerson has worked at the resort since he was a teenager.
Jared Emerson rallies the Saddleback outdoor operations team.

Soon, he and Quimby got to work on preparing to reopen, but they were barely underway when the coronavirus pandemic started disrupting life across the country. The to-do list was long and the window in which to accomplish everything was small: build a steep, hairpin, 2.8-mile gravel service road up the mountain, renovate and expand the lodge, replace the old double lift with a high-speed quad, all in less than a year. “We took something that was very hard and made it a hundred times harder with the introduction of COVID,” Emerson says.

Shepard, now Saddleback’s general manager, had to figure out how to accommodate skiers as safely as possible during a pandemic. The lodge got a new ventilation system designed to reduce risk of virus transmission — something that might not have been possible had crews not gutted the building anyway. As at most resorts this winter, lodge access is limited — skiers should put on boots in the car, and indoor dining requires a reservation. Outdoor food and bar service was added. Scannable lift tickets can be picked up at automated stations in town and on the mountain. Rentals and ski-school registration have to be transacted in advance. 

The pandemic also took a financial toll in the lead-up to opening. Sales of season passes brought in about half of the more than $2 million that Arctaris had originally projected. But Tower, Arctaris’s founder, doesn’t think what happens this year will hurt long-term goals. Over the next eight years, his group plans to invest $38 million to add more trails, more lifts, a midmountain lodge, a 40-acre solar farm, condos, and more. It’s no small endeavor, Shepard notes, but it’s being undertaken with a mind toward Saddleback’s laid-back personality. “The last thing in the world we want to do,” he says, “is turn this into a Vail of the East.”

Private-equity firms generally want to flip companies they invest in within five years, but Tower says Arctaris, bolstered by grants and donations and tax credits, can afford to be patient. “We have the opportunity to look at the fundamentals of what a ski mountain should be,” he says. “If you’re owned by a publicly traded company, you’re probably thinking about how to squeeze every last penny out of the mountain by putting condos on top of condos on top of condos. Our goals are much different here.”

Emerson admits that, growing up on the mountain, he never really considered that Saddleback might need to become more than what it was. “What we found here was exactly what we wanted a resort to offer us,” he says. “But now we have to balance the reality that this place did close for five years. We know we have to change. We’ve seen that, in the history of the ski industry, numbers rule. The more numbers you move, the more money you make, the more, the more, the more. The precious character of the place, we want more of that.”

In early December, daytime temps were still lingering in the 40s and 50s at Saddleback. It rained a few times. Then, a week before the planned December 15 opening, temperatures dropped below freezing and stayed there. The mountain got some natural snow, and crews cranked the snowmaking. On the morning of opening day, thermometers on the mountain read 18 degrees, and by the afternoon, temperatures had fallen into single digits, with a stiff wind blowing. It was cold enough for the place to shine again.