The Appalachian Trail Days Festival is the biggest event of the year in Damascus and the world's largest celebration of the Appalachian Trail and hiker culture! Each year in May, the town swells to an estimated 25,000 people for the festival. You can expect a grand reunion of thru-hikers past and present, over a hundred vendors of handmade goods and some of the best outdoor gear in the industry, a packed schedule of live music and events, and a large crowd of trail supporters and hiking enthusiasts.

​Trail Days is always the weekend after Mother's Day. The Town-wide Yard Sale is always the weekend before Trail Days. Trail Days is free to attend, with a fee for overnight camping at Tent City.