CHARLES CHESNUTT LEADS A DOUBLE LIFE.
In one, he works as a costumed historical guide on a cruise ship plying the Mississippi through the Big Easy. He’s 37, bearded, and used to be a lawyer, which becomes clear whenever he opens his mouth. But in this crowd, Charles Chestnutt is Disney, has been ever since he hiked the length of the Appalachian Trail in 2005. And Disney is a fun-loving guy.
At the moment, around 10 p.m. on a steamy night in May, as hundreds of AT aficionados are gathered a few miles from the trail at a sprawling campground in tiny Damascus, Virginia, Disney is stalking a winding path and towing a boom box that blares electric through the nearby scrub pines. “I’m sexy and I know it,” come the lyrics above a pulsing techno beat. A high, gleeful wail of synthesizers ensues, and Disney responds with a sinuous swirl of his midriff. He’s not svelte, certainly, but he is peacock proud. And he’s not alone. Behind him in a loose conga line are two dozen other revelers, each one bearing a bright-green glow stick necklace and a plastic cup of cheap beer, each one mouthing the lyrics of LMFAO’s 2011 hit. I got passion in my pants And I ain’t afraid to show it (show it, show it, show it).
The line snakes its way into the crowd, injecting its energy into the already raucous scene. This is Trail Days, a yearly coming together of the hiker tribe for four days of fun. The festival draws thousands of trail lovers and boosters—from newbie dayhikers to grizzled Triple Crowners, from gear companies to this magazine—to the southern Virginia burg for clinics, gear repair and prizes, and music. Attendees divide up by allegiance, joining one of the long- established “camps” or, for the unaffiliated, setting up in Tent City. By day—and especially by night—it’s the biggest party on any trail.
Disney represents the faction that comes here to go harder than anyone else. He’s part of a crew called Riff Raff, a loose contingent of 80 or so hikers who do Trail Days with uncommon verve. Riff Raff is a rowdy bunch, established 11 years ago and roughly 75 percent male. Members gather en masse but once a year, at Trail Days, and they subject their novitiates to a formalized initiation rite. Each worthy Riff Raffer is inducted at a “shirting” ceremony, at which he is bestowed a T-shirt, usually black, with the group’s insignia: a skull in a cowboy hat looming above a crossed set of trekking poles.
The AT has always been the social trail of the Triple Crown. Town, pizza, and beer are never far away. Shelters encourage hikers to camp in groups, and groups encourage more socializing. Historically, drinking and pot smoking have been mild phenomena on the trail, easily sidestepped by purists aiming to be at one with a trickling creek. But today, Riff Raff ’s brethren are not easily avoided. Long-haul foot traffic on the trail has doubled since 2010, now including 4,000 aspiring thru-hikers each year, many of them young and unburdened by conventional views of the backcountry experience. And there has been a culture clash.
David Miller, the author of The A.T. Guide, notes that, since 2015, nine trailside hostels and hotels have asked to be removed from his book. Many trail towns, Damascus included, prohibit hikers from pitching tents within city limits. The outcry from trail purists is mounting.
Ben Montgomery, author of Grandma Gatewood’s Walk, remembers stand- ing near the summit of Katahdin in 2012 and watching four twentysomething thru-hikers celebrate the finale of their northbound AT journey by tromping arm-inarm through a meadow of endangered Bigelow’s sedge. “They just didn’t give a shit,” Montgomery says. “If you have 4,000 people like that on the trail every year, the magic of the AT will die.”
This angst about changing trail culture seems to be directed with particular vehemence at Riff Raff. The group has been described as an outlaw hiker gang, more like the Hell’s Angels than the Sierra Club.
But if Disney is supposed to be terrorizing the other hikers at Trail Days, proclaiming his sexiness does not appear to be doing the trick. Indeed, during his stay at the festival, he will outlay some $400 buying beers for friends and strangers. And as he wends through the woods in Damascus, he is hailed and adored by Riff Raff’s counterparts—by the salty old hippies of Billville and by the crystal- healing, velvet- clad romantics of Wonderland camp. These folks, too, have vast quantities of beer laid in like cordwood against an Alaskan winter, and they rise and wobble away from their campfire and join Disney in dancing. They writhe and twist awkwardly in hiking boots, ragged shorts, and ashbegrimed T-shirts. Disney grins.
When Benton MacKaye, the AT’s founder, first proposed “an Appalachian Trail” in a 1921 essay bearing that name, he famously envisioned a “wooded wilderness” retaining “much of the primal aspects of the days of Daniel Boone.” But “community” was always part of his scheme. MacKaye imagined a trail that would connect a network of farms and camps where city dwellers could gather to unwind.
The trail and its users have of course evolved in many ways in the decades since, but one thing is clear: The AT has attracted legions of fans, many of whom have strong feelings about what is “good” or “bad” for the trail. To Disney’s people, “Sexy and I Know It” is the sound of progress, of good humans finding bliss in the wilds. As they see it, MacKaye wanted a party in the woods.
IN THE EARLY 1980s, when long- distance walking first became popular, AT thru- hikers relied on an underground booklet called “The Philosopher’s Guide.” The 1983 edition was printed in purple, on a mimeograph, and contained insights on, for example, the best trail snack food (Parkay margarine). The tone of The Guide is insidery and knowing. Reading it, one gets the sense that if serious partying was a thing back then, The Guide would have linked up a pub crawl of backwoods watering holes.
But drinking is scarcely mentioned, and the book actually tells readers to celebrate the completion of a thru-hike by swimming in a Maine lake, calling it “a perfect place for some soul- searching … a perfect place to feel the tinge of melancholy.” Andrew Downs, Virginia regional director for the Appalachian Trail Conservancy, says, “There was partying on the trail in the ’80s’ and ’90s, sure, but it was contained and selfpoliced. If you left trash, other hikers would call you out. In the past decade or so, there’s been a shift, aided by social media, into a mob mentality.”
“Cell phones and improved coverage allow hikers to better locate their cohorts and coordinate their party plans,” Dave Miller says. “I recall one hiker telling me that he was working on an app specifically for this