ARTS & CULTURE FOR THE LOVE OF MUSIC From pop, country and bluegrass to soul, rock, jazz and a burgeoning singer-songwriter scene, Loudoun is a melting pot of music genres with a slate of unique venues to match. Tune into some of our big-name local artists on Spotify’s Songs of Loudoun playlist. A STORIED MUSIC VENUE Opened as a cinema in 1931, Leesburg’s Tally Ho Theater is a marquee venue showcasing big name acts, cover bands and local stars such as My Kid Brother and Emmet Swimming. Music in the Gap FOOD, DRINKS & TUNES Vanish Farmwoods Brewery hosts original bands every Saturday and Sunday while Fleetwood Farm Winery features local and regional artists. Monk’s BBQ features crowd pleasers such as local bluegrass foot-stompers Short Hill Mountain Boys. In Leesburg, Loudoun Kitchen & Bar hosts country music line dancing each week. For more refined audial tastes, Lightfoot Restaurant features regular live jazz on Friday evenings. Sunset Hills Vineyard CONCERTS & EVENTS Many Loudoun wineries and breweries offer live music performances throughout the year. In September, the Crossroads Music Festival brings a mix of local talent and national acts to downtown Leesburg. 868 Estate Vineyards hosts the day-long LoCo Fest each fall, raising money for local musicians. Songstress Tracy Hamlin’s Sweet Jazz Festival takes place over a weekend in spring while world-renowned classical musicians such as cellist Zlatomir Fung have appeared at the Waterford Concert Series on select Sundays. Round Hill – Hillsboro Appalachian Trail Festival
Explore Loudoun Official Visitor Guide 2026 Explore Loudoun Official Visitors Guide: Page 28
