Trail Days Turns a Tiny Appalachian Trail Town into One Big, Sweaty Party

Note: This article first appeared in the Summer 2019 issue of AMC Outdoors.

A man stands at the edge of the campfire, illuminated by the orange glow of an ever-growing flame as it licks the rock ring surrounding it. I’m nervous for his safety. He has been drinking for some time now, and one wrong step could result in injury. But he maintains his balance, cupping his hands around his mouth and commanding the attention of those around him with a battle cry.

“Riff-RAFF!” he shouts, and the group echoes the call back. “We’re a ridiculous family full of personalities,” he says. “And we’re here today to welcome one more.”

He’s holding a black T-shirt emblazoned with a large skull and crossbones. The skull is wearing a cowboy hat, above which reads, “Riff-Raff,” the name granted to this family of personalities. I’m about to witness a Friday-night shirting ceremony, the initiation phase for members of this tribe—a self-selected term used to describe the many groups of hikers gathered here. It’s my first time at Trail Days, the three-day Appalachian Trail thru-hiker festival held annually in Damascus, Va. I’ve flown in from Boston with Paula Champagne, my adventure partner and AMC’s photographer, to spend the weekend among this thru-hiking community. 

The festival spans the entire town (all 0.85 square mile of it), but the place to be this Friday night is in the heart of Tent City. Here, AT thru-hikers past, present, and future flock to celebrate achievements on the trail and to catch up with friends, camping along the nearby brook and staying up late for bonfires, food, drinks, music, and more drinks. Half a mile up the road, the town’s main park is quiet—the gear booths have closed up for the night, and locals are heading home to rest—but here in Tent City, the party has just begun. 


Trail Town, USA

The 42-mile stretch of the Appalachian Trail leading into town is known as the Damascus Dash. With the promise of fresh showers, hot food, and stores where hikers can replenish their provisions, some northbound (NOBO) AT thru-hikers tend to push through this section as fast as they can. When hikers emerge from the trail into the town’s park, they pass under an engraved wooden sign welcoming them to Damascus and a day or two of rest in civilization.

It’s hard not to notice the AT’s presence here. The trail continues right through town, past shops, hostels, inns, and restaurants. Murals depicting the trail’s famed white blazes decorate the sides of buildings, while bricks commemorating past thru-hikers pave the sidewalks. Outfitter shops, hawking moleskin for blisters and fuel-canister refills for backpacking stoves, encourage hikers to stick around a few extra days and take advantage of Damascus’s other claim to fame: the 35-mile Virginia Creeper Trail.

A former railway, the Creeper Trail now attracts more than 20,000 hikers, bikers, and runners annually, in addition to the 1,386 AT thru-hikers forecasted to pass through in 2019. According to the Appalachian Trail Conservancy, about 42 percent of NOBO AT hikers who started in Georgia in 2018 made it to Harpers Ferry, W.Va., passing through Damascus; 26 percent of SOBO thru-hikers made it to Damascus. As of June 12 this year, an estimated 3,300 hikers had started their 2019 thru-hike northbound.

“Damascus has built its future and reputation on outdoor tourism,” explains Tim Williams, the town’s vice mayor and chair of the Trail Days committee. “We realized that, if you hike the AT, you have to come to Damascus, so this seemed like a natural fit.”

Trail Days is Damascus’s way of giving back, a love letter to the AT community. The idea for the festival originated in 1986, when the Appalachian Trail Conservancycelebrated its 50th anniversary. The ATC, formerly known as the Appalachian Trail Conference until 2005, was created to preserve and manage the natural beauty and cultural heritage of the Appalachian Trail. The group wanted to mark the 50th milestone with parades, music, and other events in communities all along the AT, and Damascus jumped on board. (Damascus is one of more than 40 ATC-designated Trail Communities, joining forces with the likes of Franklin, N.C.; Blairstown, N.J.; and Hanover, N.H., that pledge to host an AT-themed event or work day each year; see the map on page 31.) As the years passed, many towns stopped hosting annual events, leaving Damascus to take over the tradition and make Trail Days what it is today. 

“Damascus never quit,” Williams says. “We’re a town of 800 people, with no red lights and no marketing strategy, so it’s miraculous that [Trail Days has] lasted 33 years. The thing about this festival, though, is that it’s a reunion. That’s what makes it such a marvelous gathering.”

The festival has grown significantly over the years. Held in May, when NOBO hikers typically reach Damascus—463 miles from the AT’s southern starting point, at Springer Mountain, in Georgia—Trail Days went from about 500 attendees in 1986 to an estimated 10,000 this year. That means the town’s population temporarily mushrooms to more than 12 times its usual size. I meet locals who’ve driven from surrounding areas to see the parade, as well as current and past thru-hikers who now live in New Hampshire, Arizona, Texas, even New Zealand.

“We outnumber the town,” says a section hiker and proud member of the Riff-Raff tribe who goes by the trail name ChainE. “They’ve always been supportive of us. It’s really awesome what they do, since basically they let us come and take over their town. Most towns wouldn’t allow that.”

The town doesn’t seem to mind. When Paula and I arrive in Damascus the morning of May 17, it’s pouring. We retreat into the local diner to wait out the rain, packing in with clusters of hikers sporting mud-caked Merrells and tie-dyed bandanas. A young man with dreadlocks sits in conversation with an older woman with flowers in her hair, while a band of bearded 20-somethings asks for their check. The waitstaff zips through narrow gaps between sopping backpacks, carrying trays of bacon, eggs, and cornbread. It’s seat-yourself, and we claim an open table by hovering over the scraps of half-eaten breakfast scattered across it. One man asks me if we backpacked to Damascus. When I tell him we drove from the nearest airport, he laughs and says he wouldn’t judge us if we grabbed the leftover bacon for a trail snack later, almost as if he expects us to do so.

Despite the huge crowds, there’s surprisingly little information about Trail Days online. Most of the festival regulars I speak with say people find out about it by word of mouth, with Tent City tribes keeping in touch via Facebook and email. The Trail Days Ministry, spearheaded by Damascus resident Linda Austin, does the heavy lifting. Roughly 240 volunteers from Damascus and surrounding communities come to help out with the festivities, offering free laundry service, haircuts, shuttles around town, and the very popular foot-washing station.

“For me, it’s an opportunity to show love to people, meet their needs, and open the doors for a spiritual conversation,” says Austin, a Trail Days coplanner for the past 19 years.

Beginning Thursday night the third week of May, the Trail Days schedule is packed with speakers, including Jennifer Pharr Davis, an author and three-time AT thru-hiker who set the AT’s then “fastest known time” of completion (46 days, 11 hours, 20 minutes) in 2011. There are presentations on topics ranging from conservation efforts to practical hiking tips to ways the AT has changed over the past 50 years. There are workshops on fly-fishing, local edible plants, and navigation skills. There are pie- and hot-dog-eating contests; there is jewelry making and sidewalk art. And the list goes on. 

While the partiers mostly stick to Tent City, the town’s main park turns into something akin to a marathon expo, with gear brands showcasing the lightest weight hammocks or the latest trail navigation apps. Some booths offer free giveaways (socks, stuff sacks); others provide gear-repair services; and a few host friendly competitions (fastest tent setup). There are cotton candy and lemonade stands, plus live music and plenty of picnic tables to rest on.

Everything culminates in Saturday’s main event: the hiker parade. Participants line up with their respective cohorts—like graduation, you walk with the year you finished your thru-hike—and march down Laurel Avenue, firing water guns at the crowd. When it comes to their outfits, marchers go all out. It’s not uncommon to see a grungy hiker proudly sporting a floral prairie dress or full face paint and a rainbow mohawk. The town’s fire department loads up its hoses and joins in, celebrating the community that is Trail Days.


The Road to Damascus

I forget how I first heard about the 2,190-mile Appalachian Trail, but by the time I was in high school, I had developed a bit of an obsession. On day hikes, if I crossed paths with an AT pilgrim in New Hampshire, I’d nudge my hiking partner and whisper, “Hey, that’s a thru-hiker!” I viewed these dirty, tired, skinny, smelly humans as rock stars, elites who had the courage to take to the trail. To be among so many of them in Damascus, learning about their journeys and mistakes en route and, above all, their love for the AT, I long to be a part of it all.

It’s quiet as we walk through Tent City on Friday morning. We’ve heard stories of the parties that take place in the woods of Beaverdam Creek Park, and I assume the previous night was a blowout, given the small handful of early risers up and about, tending to their camps. As we wander the gravel path, a man nursing his cigarette nods to Paula and me.

“I got in last night,” he tells us. “I’m just soaking it all in.”

He goes by the trail name Laptop, bestowed on him by fellow NOBOs because he’s thru-hiking with his computer, always on the lookout for Wi-Fi access. “[My son’s] teacher is an avid hiker, so I Skype in with the class when I can and try to teach them about the trail,” he explains. Laptop planned his thru-hike to reach Damascus in time for Trail Days. When the weekend is over, he’ll have 1,727 miles left to reach Katahdin, in Maine. 

People take to the trail for a multitude of reasons, and some are more willing to tell their stories than others. There are those checking it off their bucket lists. Others recruit sponsors and thru-hike to benefit a charity or to spread awareness for a cause. For still others, the Appalachian Trail is a source of healing.

“A lot of the folks we’ve encountered are in recovery, dealing with mental health issues, addiction,” says Linda Austin, who also ministers to thru-hikers outside of Trail Days. “Some have lost spouses, jobs. There’s a lot of heartache out there, and the trail can be very therapeutic for a lot of people.” 

Such was the case for U.S. Army veteran Ron Sanchez, who was hiking the Appalachian Trail this year to recover from PTSD and depression, according to a May 19 article on Sanchez was fatally stabbed on the trail on May 11, the first murder along the AT since 2011. 

The tragedy happened about 50 miles north of Damascus, in the Mount Rogers National Recreation Area, just a week before Trail Days. It’s still fresh on everyone’s minds. Booths are handing out red, white, and blue ribbons to honor the fallen hiker, and parade marchers carry signs reading, “AT Strong.” Tamitha Rice, a caretaker at the popular Woodchuck Hostel, says the murder absolutely has been a topic of conversation, but she doesn’t get the sense there’s a prevailing fear keeping thru-hikers from continuing their trek north. 

“This was a random incident,” she says. “But there is definitely some PTSD for those who were close by. It’s close to home.” 

Dustin “The Dungeonmaster” Soutendijk doesn’t seem fazed by the tragedy. We encounter him at Little Bits Baking Co. & Provisions, a coffee shop on Laurel Avenue famous among Damascus residents for its cinnamon buns—a treat another passerby says is too much of a sugar rush for trail-wizened hikers, despite their recommended intake of 20,000 calories a day. 

“Being back in town is nice, but I do get restless after a few days,” Soutendijk says, as he finishes up a letter to a friend. He started the hike with his sister in April after years of dreaming about it. “For a lot of hikers, (the trail) is a catalyst for change,” he says. “You’re in your head all day, so you have time to think about the past and the future.”

Trail Days gives you the chance to see how the AT changes thru-hikers—both mid-journey and after. Back at Tent City, I meet a couple who fell in love on the trail. They seem like exact opposites: The man, who goes by the very fitting trail name of Chatty Kathy, is full of high energy and enthusiasm, plucking away at his guitar as we speak, while the woman, Sacagawea, is more calm and reserved, choosing her words with care. The two met the second week of their 2012 thru-hike and had their first official date at a Dunkin’ Donuts off-trail. He proposed to her on the summit of Katahdin, the AT’s northern terminus, where they finished their thru-hike together. They were married at Trail Days in 2015 and continue to return each year.

“We come here for the community,” Sacagawea says. “It’s not like we don’t have friends in other parts of our lives, but here people can let loose and be ourselves. You don’t have to hide who you are here. 

“The trail changes you,” she continues. “It creates this disconnect with the world. That’s why we say that going to Trail Days is going home.”


Magical Thinking

Paula and I hear it again and again over the course of the weekend: The main reason so many people come back to Trail Days each year is the community.

Maybe that’s the reason I feel an instant connection to Trail Days. Although I’m not a thru-hiker (yet), as an AMC employee and a volunteer hiking trip leader for the Boston Chapter, I spend the majority of my weekends on the trails, where I feel most comfortable, most like myself. My friends and family back home don’t always get that.

This sense of community is especially visible walking through Tent City, where signs welcome you to the different tribes around camp. Some, like Billville, named for a 2000 cohort of thru-hikers that has evolved into one of the largest groups at the festival, have been a part of Trail Days for years. Billville hosts useless-gear contests (where thru-hikers show off items that might seem unconventional, like hiking poles with training wheels) and chili cookoffs, and decorates its site with oversized dome tents and string lights hoisted up into the trees.

Others, like Wonderland and Hiker Trash, are smaller and more laid-back, composed of more recent thru-hikers. Groups intermingle, of course, and by sundown the whole campground turns into a big party. There’s an annual bonfire, hosted by the Trail Days legend Miss Janet, a trail angel for more than 10 years who helps thru-hikers by offering rides and supplies. New to the bonfire this year is a collection of overturned plastic barrels, designed to encourage a cross-cohort drum circle.

“It turns into a sort of redneck, hippie, frat party at night,” Quicksilver, a Trail Days regular, says with enthusiasm.

The town’s police are well aware of what goes on in Tent City and patrol the grounds throughout the night. Riff-Raff, possibly the largest—and definitely the loudest—of the tribes works with officers to help mitigate any trouble before it gets out of hand.

“They’re on the same page as us,” says ChainE, who led the Riff-Raff shirting ceremony earlier in the day. “They want people to have a good time but also to be safe. We have a good relationship with them, where, if there’s an incident that’s too big for us, we know they’re there to handle it.”

In between anecdotes and colorful bits of gossip, ChainE keeps mentioning something called trail magic. The idea, he explains, is that while Trail Days is a place for former thru-hikers to gather and party, it’s also a time to give back.

“We want to encounter hikers and steal them off the trail for a bit, show them a good time, and hopefully they will come back next year to pay it forward,” he says.

Imagine thru-hiking the AT, logging 20 miles a day and eating nothing but dehydrated meals, nuts, and jerky. You could really go for a cold beer, or an ice cream, or maybe you just want a hot shower and somewhere to wash your underwear. Then, as you emerge from the woods, into a field outside Damascus, you see a group cheering you on and waving you over. They have everything you can imagine: laundry, fresh produce, alcohol—and if they don’t have what you need on hand, they’ll gladly go pick it up from the store while you take a break. This is trail magic, and these gestures of support might be enough to boost your energy and keep you pushing along the trail. 

Riff-Raff members perform trail magic throughout the AT season, but during Trail Days, they really amp it up. A week in advance, those who are able to take time off work meet at a farm along the AT, near Damascus. “People take time out of their day to offer anything and everything: beer, candy, anything that feels like a luxury to hikers,” says a former thru-hiker who goes by the trail name Dead Man Walking.

Trail magic is also part of what gets you initiated into Riff-Raff. Sacagawea explains that, in order to receive a T-shirt, you need to do two things. First, you must love and have a connection to the AT, whether that’s via a thru-hike, section hikes, day hikes, or even just living on or near the trail. Second, you participate in trail magic.

“You have to demonstrate your desire to be a part of something bigger,” she says. The community support continues post-Trail Days. A month after returning from Damascus, I spot a familiar skull and crossbones T-shirt in the Instagram feed of a friend who’s hiking the Pacific Crest Trail, on the West Coast. It’s nice to know help is out there.

Back in Damascus, as the early summer sun sets over town, Tent City comes alive with tiki torches and the percussive beat of drummers. Some revelers dance in the fields, while others carve up the pig they started roasting earlier in the day. This is the moment the hikers have waited for, and it feels right to let them proceed without interruption. We decide to head out before the party really gets going, but as we’re leaving, ChainE catches up to us, two plastic orange wristbands in hand. “You’re welcome here anytime,” he says. 

I carry that wristband in my daypack now, tucked in beside my map and compass. It serves as a reminder to pay it forward, to offer a little bit of trail magic to any hikers who need it along the way.

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