Carrabassett Valley in 48 Hours

Sugarloaf’s hometown is a winter destination, but Carrabassett Valley and the surrounding towns offer outdoor recreation year-round, with miles of mountain biking trails, lakes and rivers for paddling, and some of the best hiking in the state.

Settling in and fueling up

It’s hard to imagine a wiser escape during a pandemic than the mountains in Maine. At Sugarloaf, surrounded by hundreds of thousands of acres of social distancing space, your world becomes hills, trees, and lakes. Problems reduce to the roots under the tire of your mountain bike, balancing on a rock in the river, and the distant roar of ATVs.

Glide through the double doors of the Sugarloaf Mountain Hotel, free of bulky boots and skis for once. Check in, and get back down the Sugarloaf Access Road to the restaurant and bar of snowboard-cross Olympic legend Seth Wescott: The Rack, an all-season staple with firepits and old-school chairlifts. Fill up on the BBQ Sundae—a pile of baked beans, pulled pork, and coleslaw with a cherry tomato on top—and you won’t regret it, especially before a full weekend of outdoor activities. If only there were an ice cream sundae for dessert.

A scene from West Mountain Falls Trail. 

Peaceful paddles and mountain drives

Start with a mug of coffee at 45 North, the hotel’s restaurant, and proof that ski resort restaurants have taken it up a notch in recent years. On the back patio, over French toast with maple syrup and raspberries, you can soak up a greener view of the ski trails you know. Then Ed Shevenell of Downhill Supply Company will start you off right—on a paddleboard on Flagstaff Lake in Stratton. The resort’s ski shop rents stand-up paddleboards and kayaks. Once you’re on the lake, drift off in silence at the mercy of 360-degree views of Bigelow Mountain and Sugarloaf, near the start of one of the most intense sections of the Appalachian Trail.

Flagstaff is one of Maine’s largest lakes by area, but beneath its shallow depth is an underwater ghost town. The villages of Flagstaff, Dead River, and Bigelow were flooded in 1950 to create a hydropower dam; the deeper channels are part of the Dead River, feeding into the Kennebec River. There’s not a motorized boat in sight and only a handful of houses. “The beauty of this area is that the majority of the land on the lakeshore is taken up by the Bigelow Preservation, which includes Native American land, so it really has kept people off the lake,” says Shevenell.

You’re just a half hour from Canada, which explains the Canadian flags along Route 27, part of which is called Arnold Trail after Benedict Arnold, who in 1775 brought his troops through the area to try to take over Quebec City. Mount Bigelow is named after Major Timothy Bigelow, one of Arnold’s officers.

Hit up Stratton’s Northland General Store for, according to the clerk, “what everyone’s been drinking this summer”: Tubular IPA by Orono Brewing Company. Back at Flagstaff Lake Boat Ramp, take a sip and sit in a kayak for good measure. Paddle out for a picturesque view of Bigelow’s Horns, known by the locals as the Sleeping Indian for their profile at dusk. But there’s something else in store for sunset.

Between Stratton and Rangeley, Quill Hill is well worth the 12-minute drive from Route 16 up a well-maintained dirt road to the 2,848- foot summit, for 360-degree views of Maine’s northwestern mountaintops. Flagstaff seems small now. Pink skies reign over Saddleback and Rangeley’s lakes, Tim Pond, and the Kennebago River. Quill Hill is owned by the family of Adrian Brochu, who passed away last year. They also welcome the public on the nearby Ira Mountain in Kingfield, which offers unrivaled views of Carrabassett Valley (plus an amphitheater).

Hitting the trails

It’s rise and shine, then off to Alice and Lulu’s on the mountain for a Maine ham Italian with salt, pepper, and oil to go. You have places to be, and by the end of the day, you may have a new hobby. But don’t be fooled: mountain biking is no leisurely pursuit. Rent bikes and learn about 77 miles of local trails at Allspeed at the Sugarloaf Outdoor Center.

Take your time on the trails—the scenery is beautiful. You can snap photos of the lily pads on Moose Pond, a wooden bridge, and the wildflowers framing Sugarloaf. If you follow the narrow crisscrossing trail called Grassy Loop, you may even find yourself maneuvering past other riders like a real mountain biker. When you need a break, sit down on the dusty trail and eat your sandwich. The bruises are a rite of passage.

If you prefer an outdoor adventure with both of your feet on the ground, try hiking Little Bigelow, a 6.1-mile out-and-back route; do a shorter hike up to Cranberry Peak; or, if you’re feeling ambitious, climb Sugarloaf itself via the Appalachian Trail. If there’s sunlight left in the day, tag on a stop at West Mountain Falls, a series of cascades down the Sugarloaf Access Road. To get there, drive slowly past moose crossing signs—they’re flashing—to the Sugarloaf Golf Club course and enter the trail across from the Winterstick Snowboards factory. For more dramatic waterfalls, add Houston Brook Falls and Poplar Stream Falls to your bucket list (like much of Carrabassett Valley, they’re on Penobscot Nation land).

Once you’re ready to relax, sip wine under Edison lights along the river at Stratton’s Backstrap Bar and Grill, then peruse the plants and pottery outside at the Coplin Co-op across the street. In Eustis, swing by the sweetest 1950s-style food trailer, Mandy’s Diner, at Cathedral Pines Campground when it reopens next spring (Mandy’s whoopie pie milkshakes are all the rage). Now, finish the day at Trail’s End Steakhouse and Tavern for no-frills dining with the locals. Until next time, Sugarloaf. See you when there’s snow on the ground. 

Sip a milkshake at Mandy’s Diner at Cathedral Pines Campground in Eustis. 

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