The Basics: A sleepy spec on the map in the Virginia Blue Ridge Highlands with a tiny flavorful one-road downtown. A population of around 1,000 plays host to a steady flow of outdoor-loving tourists-including hardcore thru-hikers (the Appalachian Trail runs through town) and others bed-and-breakfast weekenders.

Highlights: Known as the “Friendliest Town on the Appalachian Trail,” Damascus hosts the four-day Appalachian Trail Days Festival during the third week of May. The celebration is a nationally-renown thru-hiker reunion and ultimate party for more than 20,000 hiking enthusiasts who enjoy gear booths, lectures from footpath pioneers, live bands, and a famed parade.

Outdoor Opportunities: Damascus is the mid-point of the 34-mile Virginia Creeper Trail, a rails-to-trails cycling gem. Bikers looking for a challenge can do the steady 17-mile climb to White Top Station, or for those looking for an easier ride, an outfitter can provide transportation to White Top for a downhill ride back to town. The Creeper is also a favorite for running and horseback riding. Mountain bikers find more of a challenge on the rugged singletrack of the Iron Mountain Trail.

For hikers exploring the area, a summit of Mount Rogers (5,729 feet), the highest peak in Virginia, is essential. There are many options to get to the top (the 120,000-acre recreation area holds more than 400 miles of trails). Damascus’ Sun Dog Outfitters manager Steve Webb likes to send hikers on a four-mile jaunt on the A.T. from Elk Garden off state road 600. He also recommends heading into Grayson Highlands State Park and hiking Wilburn Ridge towards Rhododendron Gap and around to Rogers.

Good Eats: The Damascus Old Mill is a converted gristmill that has become a favorite restaurant and musical hall. The place for breakfast is Do Duck Inn, while Sicily’s has the town’s best pizza. Locals are looking forward to the new Baja Café, which will open in April.

-Jedd Ferris