Sugarloaf isn’t known as Maine’s most accessible mountain. That’s not just because of its distance from Boston and Maine’s urban centers (although it is a long drive up Route 27 to get there) but also because it’s a mountain with character, talked about in the same way my dad talked about chores and hard living building character: difficult, rough-and-tumble, and a little hairy.

Having spent a good number of my beginner and intermediate days as a skier in Carrabassett Valley, I’ve always thought Sugarloaf’s 150-plus trails had something for everyone. Over the past two years, teaching my partner how to ski at Sugarloaf confirmed it. The truth is, the Loaf can be skied from its 4,237-foot summit to its base by any skier, no matter their ability level. Sugarloaf.

You just need to know where to go.

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GO EAST

The eastern side of the mountain is home to backcountry terrain and one of the best-cut trails in New England.

The Whiffletree and King Pine quads climb up the mountain’s eastern side, starting yards from the base lodge and ending immediately below the summit snowfields. The former rises over a winding network of beginner and intermediate trails, while the latter provides access to some of the best expert terrain in the east, including side-country skiing on neighboring Burnt Mountain and Brackett Basin, which was added in the most significant expansion of the resort’s terrain over the past decade.

While the eponymous Whiffletree trail offers a freewaywide path from the lift’s top shack to its bottom, it is often crowded with legions of Perfect Turn ski and snowboard classes. Bearing left from Rollway drops skiers onto Pole Line, an underrated (and lightly trafficked) gem. Running parallel to Springboard, Pole Line is narrow—only about the width of a groomer track or two—with a string of phone poles along the length of the trail. When groomed, it’s an easy, secluded cruiser removed from the traffic under the lift. 

Until about a decade ago the Cant Dog glade, skiable off the top of King Pine, marked Sugarloaf’s eastern terminus—officially, that is. Unofficially, locals could list off a string of a half-dozen out-of-bounds trails with names like Adrenaline Rush, Hell’s Gate, and Taco Land, which dumped rope-ducking skiers and riders onto the ridge between Sugarloaf and Burnt Mountain. Over the past ten years, expansion onto the neighboring peak has opened up over 650 acres of backcountry-style cliffs and chutes in Brackett Basin, including some of this formerly verboten ground. This wild terrain is accessi – ble by either a hike or, since 2018, regularly scheduled cat skiing service. To try out the terrain for the first time, traversing the top of Cant Dog and a short hike along the Golden Road to Edger I or Edger II will provide a window to the steep, tight lines of the expansion, with the bonus of being close enough to the resort proper to cut back to the base of King Pine for another ride.

Coming off the top of the King Pine lift, a quick turn puts you onto Widowmaker—for my money, one of the most perfectly cut trails in New England. When Sugarloaf founder Amos Winter laid out trails on the mountain, he took care to place them along the fall line, only putting turns in natural flat areas before returning to the most direct path down the mountain. Widowmaker starts with a precipitous drop straight down the hill, before widening and bearing to the skier’s left. With an ample and consis – tent pitch from top to bottom, it’s an equally fun place to lay deep GS (giant slalom) turns on corduroy or to test your core when it has turned to moguls after a storm. A hard cut to the left at the trail’s end leads to Ramdown, or one can opt for Flume—an elevator-shaft drop with enough g-force to push your knees to your chest.

DOWN THE CENTER

At the middle of the mountain, you’ll find plenty of beginner routes and more technical trails near the top.

Back at the base, the Snubber, Sawduster, Skidway, and Moosecalator lifts service the beginner area around and below the lodge. It’s gentle terrain, wide and flat and perfect for learning the sport. For more experienced skiers, it’s worth the occasional run down to the bottom of Snowbrook to rest your legs and take in the terrain. If you’re staying at the Sugarloaf Inn or in a mountainside condo, this may take you right to your door.

Sugarloaf’s core (literally and figuratively) is the center of the mountain. While the area was originally serviced by the base-to-summit Sugarloaf Gondola, the Double Runner lifts and Skyline Quad now work in tandem to cover the guts of the resort. Double-barreled Double Runner accesses mostly beginner and easy-intermediate terrain from its two unloading spots, making it the perfect next step for those honing the fundamentals. From the top of Skyline skiers can access any trail on the mountain, save those on the summit, from beginner-friendly Timberline to doubleblack runs Bubblecuffer, Boomauger, and Gondi Line.

Sluice, a rolling cruiser accessible from either Skyline or the long side of Double Runner, sits firmly in the Goldilocks zone of Sugarloaf’s intermediate terrain. A bit more forgiving than neighboring Spillway (and lacking the lift-borne audience), it’s vertiginous enough to offer some thrills without putting your heart in your throat. Crosscuts to the east and west along the length of the run provide easy egress to other trails, meaning Sluice can be either part of a journey or the whole thing.

The first trail carved into the side of Sugarloaf remains one of the best. Turning left at the top of Skyline and skating along the Spillway X-Cut, bypass the Sluice Chute to reach Winter’s Way. Named after founder Amos Winter and laid out by the famous Sel Hannah, the trail winds nearly 2,000 vertical feet from Sugarloaf’s summit to its base. Rarely groomed, it’s a New England classic—narrow, steep, twisty, and littered with moguls the size of Volkswagens. While it occasionally breaks Amos’s cardinal rule, cutting across the fall line at points, it’s a blast nonetheless.

GET TO THE TOP, FAST

Rides up Superquad and Timberline will bring you to the summit and to popular racing trails

The SuperQuad, one of Sugarloaf’s two high-speed detachable quads, is a quick, comfortable path to most of the mountain’s terrain. The longest, fastest lift in the East when it was installed in 1994, it’s still the key to putting the most vertical on your skis in as little time (and as few runs) as possible. From the lift’s top terminal, you can hit the bulk of the mountain’s terrain, or trek to the King Pine, Timberline, or Skyline lifts to reach even higher ground.

Three popular trails for races and competitions sit below and on either side of the lift: Narrow Gauge, Comp Hill, and Skidder. Hayburner, to Skidder’s west, offers the same pitch and roll without gates or a timing clock. Falling away from Pinch to the skier’s right, Hayburner weaves through wide turns hither and yon, while its neighbors are unbending from top to bottom. Typically immaculately groomed, the trail can provide an early morning shot of adrenaline after the SuperQuad begins to turn. Neighboring King’s Landing (named after former owner King Cummings) is a kid sibling to Hayburner, following a parallel route with a slightly more forgiving grade.

In 1998 the Timberline Quad was installed, providing access to Sugarloaf’s peak after the retirement of the famed gondola. Unloading from the lift just below the summit, the opportunities are endless; there’s no trail on the mountain that can’t be reached from this point.

A quick left puts skiers on Tote Road. The longest trail on the hill, the intermediate run moseys for three-and-ahalf miles, heading west from the treeline before swinging back toward the lodge below Bullwinkles. For any skier who has progressed from green circles to blue squares, it’s an approachable route with a gentle slope from top to bottom. It’s not without challenge—Chicken Pitch, a quick drop in otherwise docile terrain, can spook new skiers about two-thirds of the way down. If that’s too daunting, a “Friendliest Way Down” recommended by the mountain stitches together Timberline, Scoot, and Windrow to make a green run from summit to base.

WINTER WONDERLAND

When there’s fresh snow on the mountain, head to the Snowfields at the top

On a clear day after fresh snow, there may be no better place on earth than Sugarloaf’s snowfields. You know them before you ski them—they’re that white cap that sits atop the resort’s familiar blue logo. The front face—White Nitro, Powder Keg, Bubblecuffer, Gondi Line—can be skied from the lift, while access to the backside requires a short hike to Sugarloaf’s 4,249-foot peak. Starting above the treeline, the world falls away below you as you move away from the lifts, noise, and people of the resort. While the chutes and routes on the backside have names, the beauty of the snowfields is that you can roam freely. For first-timers, it’s best to stick to High Rigger, which hugs the boundary line. The runout back to King Pine affords a look up toward Pure Heat, Jagger, and the other snowfield trails, which get steeper as you move toward the front face.

WEST SIDE SKIING

For a fun, straight shot down the mountain, head west

Breaking off at a right angle from the rest of the resort, the West Mountain chair charts a long path from the Sugarloaf Golf Course up to Bullwinkle’s, the midmountain bar and grill. There’s really only one trail on this chunk of the mountain, which shares its name with the lift. West Mountain plays out in the shape of what my Econ 101 professor called an inverted yield curve—steep up top and flat at the runout, with a long, gradual transition in between. It’s a straight shot that’s quite fun to ski, especially in late afternoon when it is bathed in sun. The biggest strike against the trail has always been the lift, a slow-moving double that crawls even if loaded at the midstation. However, this is set to be remedied as part of Sugarloaf’s ambitious ten-year plan, Sugarloaf 2030. A 450-acre expansion will add more snowmaking, new beginner and intermediate trails, additional real estate, and, yes, a new high-speed chairlift.