Apres-Ski Vibes, Year Round

Sugarloaf is the center of skiing in the Northeast, but more people are waking up to its summertime charm
Words By Jennifer Wolcott
Photos By Alexandra Roberts

Sam Punderson grew up in Vermont and had no intention to live anywhere else—that is, until he met his soon-to-be-wife, Kate, and she lured him back to her native Maine. She had left her heart in Carrabassett Valley, home to Sugarloaf Mountain, and hoped the area would win over his heart, too. Turns out, it didn’t take long for Sam—like Kate, also a lifelong skier—to become smitten. That was 20 years ago, and he hasn’t looked back from the Bigelow Range to those Green Mountains since.

In a “Love Letter to Maine,” published two years ago in Maine magazine, he wrote glowingly of the state’s finer features: “The rivers are more wild here, the lakes more plentiful, and the woods deeper,” and also of his preference for the western mountains over Maine’s much-beloved beaches and coastline.

Sam is far from the only one who’s fallen hard for “the Loaf,” which has long been a wildly popular ski destination, especially among denizens of Southern Maine, earning the area its other nickname, “Cumberland County North.”

The Secret is Out 
Sugarloaf is not just for skiers but for outdoor enthusiasts of all kinds and in all seasons. With stunning views in every direction, plenty of peaks and ponds, and trails galore, Carrabassett Valley is also one of Maine’s hottest destinations for mountain biking, hiking, fishing, boatingor just for smelling the wildflowers. It’s no wonder that the team at Mountainside Real Estate has been busier than ever selling not only slopeside condos but also single-family homes for year-round living 

But in recent years, activity in Carrabassett Valley hasn’t been limited to the slopes. A building boom of not only mountainside ski condos but also single-family homes and an exploding real estate market is keeping Sam and his team at Mountainside Real Estate busier than ever.

More winter vacationers are deciding to linger longer, and some are even putting down year-round roots in this pristine countryside of tall pines and panoramic peaks that’s only about 130 miles northwest of Portland, Maine’s largest city, and a rather ideal spot to stretch one’s legs and grab a bite on the drive up.

Word is indeed out that Sugarloaf is not just for skiers, but that the area also offers plenty of opportunity for off-season adventures. One can explore seemingly endless mountain biking trails, hike one’s pick of 4,000-footers, golf at the world-class Robert Trent Jones Jr. course, and boat and fish on Flagstaff Lake. Adding to the appeal are solid schools (including a highly regarded ski academy), an evolving restaurant scene that includes local favorite Rolling Fatties in Kingfield, which some say serves the state’s best burritos, and a cozy French wine bar, Alice & Lulu’s, that’s open all year and the perfect spot not only for après-ski, but for après anything.

A Feast for the Eyes
From the West Mountain neighborhood (top left), which offers the highest-elevation living on Sugarloaf Mountain, to Burnt Mountain Trail (middle right), and of course from the slopes of Sugarloaf, take in awe-inspiring 360-degree views of the surrounding peaks.  

“During the 20 years that we’ve lived here, there’s been a shift in year-round activity,” says Sam, who started out as a teacher at Carrabassett Valley Academy (CVA) before joining the team at Mountainside Real Estate eight years ago. “We were always surprised that it was not busier during the summer and fall months. We would take the boat out on Flagstaff Lake and have the parking lot to ourselves. Now it’s hard to even find a space.”

He attributes this partly to surging interest in outdoor pursuits, especially since the start of the pandemic—also a contributing factor to the recent flurry of property sales in Carrabassett Valley.

From spring of 2020 to June of this year, the market shot up 75 percent, he says. “During Covid, many people moved to Maine for the first time, and a large number of them had the means to buy a second home here.” Also, he adds, Mainers who were traveling more within their own state discovered the area, were taken with its staggering beauty, and chose to purchase land or an existing home.

“Just in the last three years,” says Sam, “about 20 homes have been built here, whereas in the previous 10 years, only 4 or 5 homes were constructed. People are less condo-centric than in the past and want to find an existing single-family home or build one.” That said, he adds that plans for 2023 include construction of 200 mountainside ski condos, as the market for slope-side housing is always strong and often a life-changing entrée into life at the Loaf.

Campers at Myers Lodge West on the shores of Flagstaff Lake savor a bit of solitude on the trail.

That’s been the experience of the Espinal family. Since moving to Cape Elizabeth five years ago, they have skied every winter at Sugarloaf. In 2019, they finally bought a mountainside condo, where, during Covid, the five of them, including three kids, ages 7, 5, and 2, hunkered down. Then earlier this year, they sprang for a single-family residence that Sarah Espinal says is their “forever ski home.”

Is full-time life in the Loaf next? “We’ve entertained it,” she says. Until then, they will keep making the most of winters in the Valley, where their two older kids take ski lessons at CVA, the little one will soon follow, her husband, Dan, is into ski touring (traveling uphill on skis) and fat-tire biking, and they all feel very connected. “We love the community most of all,” she says. “There is a very special energy here.”

The setting sun illumines Flagstaff Lake, Maine’s fourth largest lake and a busy summertime playground for boaters, swimmers, and fishers.

Sarah is not alone in her sentiments. What the area might be lacking—a major supermarket or its own farmers market (the closest one is in Farmington), for example—it more than makes up for with its strong sense of community and small-town character, say residents.

For Sam, Sarah, their families, and countless others who have fallen hard for life at the Loaf, the town of Carrabassett Valley’s motto, “From here on your life will never be the same,” clearly rings true.