PHOTOS: Justin Cash

Captain America stands six feet two inches, wears a flat cap, collects totem poles and keeps a vintage Sugarloaf gondola hanging outside his house in Carrabassett Valley, Maine. In 1969, the mustachioed 64-year-old—who occasionally goes by pseudonym Peter Roy—was a bartender at the infamous Red Stallion Saloon, the rowdiest ski bar in the East at the time. In 1985 during the Boston Ski Show, he ran through the city in a gorilla suit, drinking Boone's Farm wine with a Sugarloaf sticker on the bottle to promote his hometown mountain. When a policeman stopped him and told him he couldn't drink in public, he replied, "I'm a gorilla, I can drink wherever I want." And they let him go.

Which is what you do with people who are half out of their minds, living on a higher plane, born at the right time in the right place and are, as they used to say, freaking. In the 1960s and '70s, just about everyone in Carrabassett Valley was freaking—over the sugar-topped 4,237-foot massif in their backyard. For more than a century, the second tallest mountain in Maine had been the domain of loggers and trappers. After Amos Winter and a handful of the "Bigelow Boys" cut Winter's Way down its north face in 1950, it morphed into the social and winter sports epicenter of The Pine Tree State. A decade later—after an anarchic, counter-culture revival at Valley Crossing—Sugarloaf's reputation transformed once again, becoming something of a national phenomenon.

John Ritzo “freaking” in a recently gladed, hike-to terrain of the Brackett Basin zone on Burnt Mountain.

Legends don't come easy in the Northern Kingdom. It takes three generations born in-state just to call yourself a local. This is the land of VHS rental stores, $3 Italian sandwiches on hot dog buns, and Thursday night bingo at the firehouse. Backwater convenience stores smell like manure and sell crawlers, stump grinders and stacks of Megabucks tickets. People don't talk about real estate in these parts. They talk about work, and when the work's done they like to raise hell.

Raising hell became a profession for characters like Captain America, Groovy Garbage, White Trash and about a dozen other "Bad Actors" who started skiing Sugarloaf in the 1960s and '70s. Wet T-shirt contests at the Stallion were legendary. Parties at the town dump—where Captain America famously flew off a jump locked inside a refrigerator—went all night and for a few days afterwards. Jud Strunk—a regular on Laugh-In who appeared on "The Tonight Show Starring Johnny Carson"—and the "Sugarloaf Boys" comedy troop rose to regional fame while Judson's Motel, The Bag, and Chatteau de Taig rocked off their foundations every Friday and Saturday night that the snow flew. Sugarloaf's status was cemented in the November 1969 edition of Playboy magazine—that ran a spread of one of the dump parties, calling Carrabassett Valley out as one of the greatest party centers in the world.

The mountain's stats didn't create the happening, but they didn't hurt it, either. With 2,820 feet between the summit and base, Sugarloaf has more continuous vertical feet of skiing than Crested Butte, Taos, and Squaw Valley. It has the longest continuous vertical of any resort in New England and is the only mountain in the East with natural snowfields on the summit. In 2011, it features 146 trails and 15 lifts and was one of the few resorts in the U.S. to host two World Cup events.

“Jeeeezum, I’ll tell you what, that mountain up there is The Loaf.”

The afternoon I drove north from Portland, great white plumes of steam rose from a paper plant on the side of the road, obscuring the horizon. Electric candles glowed inside a row of white clapboard houses in Kingfield—gateway to Carrabassett Valley. By the time I made it to the Sugarloaf Inn, the Captain and his posse were already gathered at the end of the Shipyard Brewhaus bar. They'd come to watch their old friend Uncle Al play music, and share old stories and even older jokes. Their wives and girlfriends circled up nearby. The Bad Actors—aka Sugarloaf Boys, Curmudgeons, Locker Room Gang—are the kind of people you can't keep apart. Not by marriage, not by law. Death is about the only thing that will separate them, and hardly that, I see, as they reminisce about their old friend Strunk—singer, skier, showman, and ringleader of the '70s set who died in a plane crash in 1981.

Uncle Al—himself immortalized in an iconic 1960s photo, holding a bottle of Jack Daniels outside a shotgun shack—wraps up the night with a cover of Strunk's first Billboard Top 20 song: "Daisy a Day." When the whole bar sings along, you get the idea that people at Sugarloaf—people in Maine, perhaps—stick together. Their voices conjure the old ski bum himself and the good old days and things that were important and probably still should be. When the chorus hits, you think that maybe somewhere in the world, right here in fact, things never change.

In addition to groovy tunes, the famed ski lockers of The Loaf add to the communal vibe.

Yet something is changing. Something big. Not in the bars or in town—but something right here on the mountain. In one of the more brilliant administrative, and marketing, moves in the last 50 years in U.S. skiing, Sugarloaf is doubling its terrain. Doubling. Mountain Ops isn't cutting new trails; it isn't adding lifts. Instead, the resort is simply thinning adjacent 3,595-foot Burnt Mountain to make 650 acres of sidecountry terrain—including 2,000 vertical feet of chutes, cliffs, snowfields, and glades.

Dubbed "Brackett Basin," the expansion follows a trend in the East—along with Jay Peak, Stowe, Smugglers' Notch, and Cannon—to diversify terrain (and make the East more like the West). The questions the old codgers and half the town are pondering are how will it change the Sugarloaf everyone loves? Will it bring more people? Will taxes increase? Will there be enough snow to cover the terrain? Will the old guys get pushed out? What run do you ski first on a powder day?

The questions circulate because old people and old places don't like to change. Especially ones set in the middle of nowhere. That, and the fact that as of 2013, the redheaded stepchild of Northeastern skiing will be the largest ski resort east of the Rockies.

The old boys like to talk, so we find a quiet corner in Bullwinkle's mid-mountain lodge the next morning and sit down for a gam. Any one of the four men at the table could talk for two days about Carrabassett Valley and not scratch the surface—or lose your interest—but nobody talks when John Christie is around. Because he is the elder, the jester and scribe, who literally wrote the book on Sugarloaf's history.

From the beginning, Christie says, the mountain was run like a country club. People who wanted to ski joined the Sugarloaf Mountain Ski Club, then later bought shares in the Sugarloaf Mountain Corporation. In the summer, they cut trails; in the winter, they boot-packed the slope in return for a free half-day ticket. Five hours from Boston, few thought The Loaf would ever become a destination resort. So it developed differently than most ski areas—focusing more on what locals wanted and less on what would turn a profit.

By the mid-1960s, the mountain had five T-bars and a handful of new trails. A crew cleared a path for a flagship base-to-summit lift before stockholders had decided what the lift would be. It turned out to be a four-person Polig-Heckel-Bleichert gondola that rose 2,350 vertical feet. "The Mighty Gondola" put Sugarloaf on the national stage in terms of vertical feet and skiable acreage. In 1967, the mountain hosted the NCAA Intercollegiate Skiing Championships, and in the winter of 1971—a year when Europe received practically no snow—the mountain hosted the World Cup on Narrow Gauge.

Uncle Al and Kenny on stage setting the mood for fireside gam at the Sugarloaf Inn.

The "Tall Timber Classic" thrust Sugarloaf into the limelight, as skiers like Gustavo Thoeni, Annie Famose, and Karl Schranz raced down the mountain. The attention helped the Sugarloaf Regional Ski Educational Foundation, precursor of Carrabassett Valley Academy (C.V.A.), gain momentum. C.V.A., now an ace high school ski academy, has since turned out 11 Olympians, 10 Winter X Games competitors, six world champions, and 83 national champions, including Bode Miller and Kirsten Clark. It also sparked the Sugarloaf Mountain Corporation to begin building the mountain out to what it is today—a 1,600-acre ski resort, where luminaries like Greg Stump, Jeremy Jones and Seth Wescott cut their teeth.

Don Fowler, who's skied the resort practically every day its been open since he was a teenager, ordered a round of beers as he, Christie, and Roy spun yarns about Amos Winter's general store, the few valiant women who braved the early days, and deer hunting from the gondola. Most of the group claimed they'd never been inside Bullwinkle's bar. The old guys don't do fancy. They pack their own lunch and usually their own booze. The lodge was rebuilt in 2008 by Boyne Resorts, Sugarloaf's owner since 2007. Boyne unveiled Vision 20/20 last year—a 10-year improvement plan that includes 500 new snowmaking guns, four new lifts and, possibly, a new base-to-summit lift. (Since the gondola was decommissioned in 1996, skiers have to hike to access the summit.)

The crew has a glow on by the time we hit the slopes two hours and two pints later. I almost get around of applause when I pick up the tab and have to skate to catch up out on the slope. The Bad Actors ski like old men down the Loaf's longest trail—Tote Road, at three and a half miles—except for Christie who points his boards straight downhill and makes a half dozen turns to the bottom. Then he says he has to meet someone. And with a wave of his pole, they're all gone.

It was only noon, so I decided to take a few more runs and check out the new terrain. Brackett Basin is opening in three phases. Last year, Phase I cleared 270 acres of glades along the eastern boundary of the resort. Phase II will open 135 acres of terrain directly on Burnt Mountain this season, and Phase III will clear the north face of Burnt and another 250 acres of glades below.

Who knew a hike-to natural snowfield on the summit of Sugarloaf would act as a scene in Big Buck Hunter?

It was windy and icy at the top of the mountain and the access gates to the new terrain were closed. I ducked the rope anyway to get a glimpse and cruised along a crosscut to the top of a steep ridge. What you can't see from the resort is just how big Burnt is. Wind scoured the barren snowfields on the summit as I scoped dozens of lines that will someday cut through its thick canopy. Across the basin, there was everything from steep faces to gradual slopes wending through the birches. Halfway down the mountain, a cliff band extends around much of the bowl. It's small by Western standards but has enough airs and breaches for a season's worth of exploring.

The Phase I glades were well-spaced and I made long, lazy arcs between the pines for a few hundred feet. There was a bit of leftover powder under the trees and a mini pillow line of wide, smooth boulders. Near the bottom, I skied through a small draw and, for a moment, forgot where I was. The reality being, skiing the East is a relatively monotonous affair, and this was the most diverse terrain I'd encountered in some time. Like any skier, the thought that kept echoing in my mind as I headed back to the lift was how good it will be when the snow fills in.

At first glance, with his technical outerwear and fat tele skis, Chad Coleman looked like the anti-Christ to Sugarloaf's old guard. But after speaking with the blue-eyed 35-year-old for a few minutes, it became apparent that he was, in fact, their reincarnation. I met Coleman in the morning, in a slight daze after being drunk under the table by the Bad Actors for two days. He told me he grew up in Farmington, that his mother was a ski instructor at Sugarloaf and his father a patroller. He was a junior patroller for a while, then a sea captain, then a senior patroller at Sugarloaf for 12 years. Now, his pregnant wife announced, he was going to be a father.

Maine grows 25 percent of North America’s blueberries. Here, Matt Tinker harvests Sugarloaf’s sweet pow in the Brackett Basin Glades.

In the midst of Carrabassett's intense racing scene, Coleman somehow opted to ski powder and tree lines instead of gates. He explored Sugarloaf's boundaries for years and when he got bored of that, he and some friends started covertly cutting trails on the backside. They cut a dozen trails over 15 years and even built a little cabin called the Salsa Shack. They did it to make the mountain more interesting and take advantage of its untapped vertical. Little did they know their efforts—casually contested by Mountain Ops (who burned down the shack last year)—would be the precursor for one of the largest expansions the East has ever seen.

Coleman told me about his current post, managing the Big Mountain ALPS Program at C.V.A., as we rode the King Pine Quad. ALPS is a full time high school program that puts kids on the slopes of La Grave and hut trips in Oregon—and may well be the most innovative, coolest high school in the country. He recounted a few of the adventures as we skied to Brackett's access gate and sidestepped up a ridge that leads to Burnt Mountain. In a clearing 30 minutes later, he pointed his pole toward the manifestation of his and his friends' dreams—650 acres of Burnt Mountain backcountry the resort was now clearing for them.

The basin's layout is more complex than it looks, Coleman explained as he skied into what looked like a green cloud of pine needles. Beneath the thick canopy are valleys, rock faces, berms, and waterfalls. It's wild country, he added as we slid past a pair of bobcat tracks, where you can get cliffed-out or stuck in a ravine if you don't watch out. The big variable, he said, is whether the terrain will get enough snow. The glades will help protect it from Sugarloaf's notorious winds, of course, and they might even trap snow from the resort's snowmaking system.

Matt Tinker finds a little awesome in “Awesome.”

We dropped into an uncleared section of Phase II on bulletproof ice, scratching through natural growth, hanging onto limbs, skiing backwards through slots in the trees, and side-slipping cliff faces. The slope was steep enough that I really didn't want to catch an edge, and would be epic with two feet of powder. My tips and tails nicked rocks and stumps, but I managed to scoot down a banana-shaped chute into a clearing. The snow was softer there, and we linked 20 turns down and over a rimed ridgeline to a crosscut.

We ended up in a birch forest at the bottom and made a few turns toward the Whiffle Tree lift, where skiers were lining up for a ride. I wondered if they knew what we'd just skied, what we'd seen, and if they understood the possibilities of Brackett Basin. No matter, I figured, as Coleman waved his pole and disappeared toward the base area. They'd know soon enough and when the first big dump came, they'd never forget it.

It may as well have been 1969 that night at Sugarloaf's 60th Anniversary party. Groovy, the Captain, and Stub Taylor—who helped cut Winter's Way and every other run at Sugarloaf since—cut up the dance floor long after I sat down. Halfway through the ceremony, John Ritzo announced that Kate Webber Punderson—daughter of longtime Sugarloafer Peter Webber—would take over as headmaster of C.V.A. The shift was another link in the lineage that has kept Sugarloaf close to its roots over the years.

The next night was my last and I went to The Rack to escape the Bad Actors and dry out for a few hours. Jud Strunk's grandson, Mason, sat on the stage and tuned his mandolin as the crowd filtered in. His father, Jeff, is co-owner of the bar and told me the kid was a virtuoso. At 12 years old, he'd already played with bluegrass legends David Grisman, Jonathan Edwards, and Buddy MacDonald.

Free pony rides at The Rack.

The bar was decorated with surfboards, ancient GS skis, license plates, and dead animals mounted on the wall. The local crowd comes on Sundays to avoid the mobs of tourists who flood the place the rest of the week. An older couple held hands at a table behind me as Mason lit into his first tune—accompanied by Steve Prince, a Jackson Holer who still wears his J.H. Air Force patch on his sleeve.

The crowd hummed along, and a couple two-stepped between the tables. It wasn't just the fact that Mason was playing at his dad's bar that got everyone misty. It was the fact that his dad's dad stood on many similar stages around the valley, and the kid's presence was proof that the circle was still circling, and all of this fun in the snow really meant something.

After Mason's set, I wandered outside to chat with the local crew. Some were from away; a few had lived in the valley all their lives. We sat in the old gondola on the porch—a sister ship to Captain America's—and drank the cold away. The trails looked blue in the moonlight as snowcats rolled up and down the slopes.

It was comforting to know that the scene wouldn't change much after the expansion. There are no plans for a day lodge, lifts or grooming in Brackett Basin. You'll have to traverse and hike to ski the terrain, and get yourself out if you get into trouble. Besides being able to ski the mountain's backcountry, not a hell of a lot was going to change at all. Which, right then anyway, seemed just how it ought to be.

This story was originally published in the December, 2011 (40.4) issue of POWDER.