Sugarloaf: Luxury Comes To A Traditional Maine Mountain

A four-hour drive north from Boston takes you deep into the thick woods of remote Western Maine. Passing “Moose Crossing” signs and vintage A-Frame ski chalets covered in a foot or two of snow, you come around a corner and suddenly see a massive ski mountain. It’s Sugarloaf, looking for all the world like a three-dimensional trail map. The view is so arresting that locals call this the “Oh My God!” corner. It’s rare to take in an entire ski mountain with just one glance. In this case, it happens to be Maine’s tallest ski mountain at 4,237 feet, a genuinly awe-inspiring sight.

Sugarloaf is anchored by the town of Carrabassett Valley, which is scattered at its base, tucked into pockets of woods, and linked by a few roads wide enough to handle the logging trucks you frequently encounter in this part of the state.

Surrounded by wilderness, and a mere 37 miles from the border with Quebec, Sugarloaf is quirky, rugged, and fiercely independent, even though it has been owned by Boyne Resorts (think Big Sky) since 2007. It’s also enormous by Eastern standards, one of the largest resorts in the Northeast, with a vertical drop of 2,820 feet that rivals that of Colorado’s Copper Mountain. It also has the only lift-serviced above-treeline skiing east of the Rocky Mountains.

As a ski mountain, Sugarloaf feels an awful lot closer to a western ski resort, maybe one you’d find in the Canadian Rockies, light on development, surrounded by expansive wilderness.

This mountain has long had clusters of condos and townhouses, scatterings of private homes, and comfortable lodgings like the Sugarloaf Mountain Hotel, which has exceptionally friendly service, good food at the restaurant 45 North, and a blessedly short walk to the lifts. Apart from the base, lodging is tucked into the wooded areas, small mini-communities that feel private and quiet, and compared to most ski mountains in the northeast, a reminder of the early days. Even so, Sugarloaf is not without its luxe touches, not when there’s a challenging Robert Trent Jones Jr. designed 18-hole golf course that’s ranked the best in the state.

West Mountain Expansion

Yet there’s change afoot here at “The Loaf,” as locals call it, as a luxury home neighborhood called Dutchman Woods is rising around the West Mountain expansion. It’s opened in stages, starting in February 2024, and continuing with the newly opened Bucksaw Express lift, which provides direct access to 12 freshly cut beginner and intermediate trails.

In the first of several phases, Dutchman Woods released 20 home sites in 2024, with 17 going under contract in less than one year. They have sweeping views and large lots with ample privacy. A few multi-million-dollar homes already have broken ground.

The West Mountain Expansion is exciting because it offers skiing on wide trails that feel more like the ones you’d find out west. It’s as if you’ve been transported to the Rockies, with panoramic views of the Bigelow Mountains and an overall big mountain feel to the ski experience. Your views stretch clear into neighboring Canada, with snow-draped mountains going on for miles. It’s a luxury play that some say has been long overdue at Sugarloaf. Those with deep pockets who love the mountain are already stepping up.

Yet the good news for traditionalists is that Sugarloaf is not in danger of losing the unique character that its loyal skiers love about it. For all of the new glitz and glamour that may be coming to the mountain, Sugarloaf is a real throwback, a ski mountain that grew organically, with a town, Carrabassett Valley, created by those who loved to ski there. In her new book, A Town Built by Ski Bums, Virginia M. Wright, a longtime writer for DownEast magazine, says that the “two dozen ski bums who founded the town in 1972 laid out a vision for an outdoor recreation economy achieved through creative investment, and townspeople have focused unwaveringly on pursuing that goal ever since.”

She’s on the money, and you can feel it at every turn. There’s camaraderie, friendliness, and community here among “Sugarloafers,” as the locals and the ski faithful are known, tough to find in most ski towns today. Workers at the resort have name tags that declare “Sugarloafer since (fill in the date).” Locals and ardent guests who’ve skied here for years mark their tenure in decades, and among the Sugarloafers, there’s an outspoken sense of ownership and commitment.

After a chilly morning on perfect corduroy runs, I found that feeling in Bullwinkle’s, a day lodge on the mountain, and at après ski drinks at the Widowmaker Loft. But it was most evident at The Rack, a venerable ski bar and restaurant, with myriad rooms and a cluster of artifacts nailed to the walls and ceiling, from surfboards and skis to a lone gondola car, with live music and lively crowd. I was reminded of the refrain from theme song for Cheers, “Where Everybody Knows Your Name.” Loud and raucous on a busy night, it’s a throwback to a living 1970’s ski vibe. It’s also struck me as an indicator of respect between Boyne’s corporate culture and the free thinking locals who built this resort, a rarity at any North American ski resort in the 21st century.