Beginning in 1987, for three days each spring, 20,000 hikers descend on the sleepy burg of Damascus, Virginia, population 802, for Trail Days, the Appalachian Trail’s largest annual festival. Part Burning Man, part Camino de Santiago, part Fringe Festival thrown in for good measure, Trail Days is 72 hours of hiking mayhem. There are vendors, film screenings, book signings, and lectures. Thru-hikers either try to plan their start times such that they walk into Damascus on their own two feet, or they hitch rides and pay for shuttles. Many alums come back year after year for the marathon bonfires, the garish parade (above), the endless free junk food and trail magic. It’s where more than a few marriages have begun (and some have ended in spectacular fashion). It’s also a big boon to a community that watched the lumber boom come and go and has struggled to remake itself every since. “Damascus was really suffering from the loss of jobs,” says Suzanne Lay, executive vice president of the regional chamber of commerce. “Trail Days is a bigger boost than any of us would have thought possible.”
Local residents look on as Miss Trail Days 2017, Morgan Wolf, along with 2016 Teen Miss Trail Days Ally Manuel, Young Miss Trail Days Audra Larson and Junior Miss Trail Days Kendra Harding lead the annual parade. (Not pictured: Petite Miss Trail Days, Mini Miss Trail Days, and Toddler Miss Trail Days.) For 20 years, the pageant was a defining event for the town of Damascus but was canceled this year due to low contestant entries.
Dubbed “Trail Town USA,” Damascus is intersected by seven trails of note, including the Appalachian Trail, the Trans-America National Bicycle Trail, and the Virginia Creeper Trail. Each year, it attracts thousands of cyclists, kayakers, and hikers, who provide the bulk of Damascus’s economy. “Anytime we have people like that come into town, it makes a real impact on the whole county. We need that,” says Suzanne Lay, executive vice president of the Washington County Virginia Chamber of Commerce .
No one remembers how the tradition of dressing in drag for the annual Trail Days parade began, but it’s grown each year. At last year’s prom, a guy dressed in drag won the award of Prom Queen—a highly coveted title on the trail. Pouring rain had little effect on this year’s couture, which included poodle skirts, tutus, and dozens of men each wearing a Romphim, the viral sensation conceived by four Northwestern University undergraduates earlier this year.
Kids from towns all around Washington County, Virginia, line up hours before the annual hiker parade, many in the backs of pickup trucks with multiple super-soakers and buckets of water among them. Parade instructions on the Trail Days website are clear but rarely followed: “Reminder–NO water balloons, but super soakers are very much encouraged! Please do not spray anyone preceding the hikers, including those in uniform such as the Honor Guard and Police, or other parade participants such as trail maintenance clubs, beauty queens, and scout troops... unless they have a water gun too!”
Free love, drum circles, and shared psychedelics make a comeback once a year at Tent City, where hikers set up camp. This year, after three days of deluging rain, the field (which serves as the town’s baseball diamond and grass parking area most of the year) rivaled those of Woodstock for sheer volume of mud and soggy people. During a brief break in the storms, one thru-hiker is caught turning over her tent in an attempt to drain out the water.
Frank Masters, aka Sunset, is one of only a handful of people who can boast a double triple crown—hikers who have completed thru-hikes of the Appalachian, Pacific Crest and Continental Divide trails, not just once, but twice. He and three-person crew (pictured here without Masters) spend most of the festival holding court at Camp Sunset. This year, the four men celebrated their 69 birthdays and the fact that they all graduated college together in 1969.
For many thru-hikers, most of whom have been on the trail for a month or so, the notion of “trail family” can begin to eclipse the ones they left back home. People tend to partner-up and assume the role of “Trail Spouse,” which is sometimes platonic and sometimes not. This social bond is powerful: hikers will take zero days in order to allow family to catch up or even backtrack to find them. Trail Days, which occurs at mile 463 of the 2,180-mile trail, is one of the first places hikers have to reconnect with family they met from Georgia to Virginia.
On the final evening of Trail Days, as visitors got dolled up for hiker prom, word spread through Tent City that a pair of thru-hikers who had met on the trail two months earlier were getting hitched. By the time the bride (who goes by the trail name Extra Virgin) walked down the makeshift aisle, a large crowd had formed. The groom (trail name: Carny) was waiting for her on the rocky banks of Laurel Creek.
Thronged mostly by cheering strangers, the couple briefly exchanged vows, shotgunned two beers, and walked off into the literal sunset.
One Way Ministries, a Christian Church in Damascus, serves as the home base for evangelical churches around the country who arrive to provide haircuts, clothing repair, showers, foot massages, and meals for hikers as part of their missionary work. On rainy days, the church playground becomes a makeshift laundry line for hikers’ already funky clothes and gear.