The Crossroads Music Festival in Leesburg, VA, is more than just a music event—it’s a heartfelt community showcase of original music that benefits local children’s charities. Organized by the nonprofit BENEFIT, the festival brings together local venues and songwriters in bustling downtown Leesburg to raise awareness and funds for nonprofits serving children throughout Loudoun County.
Held over two evenings in mid-September, the festival spans both intimate concerts and free neighborhood showcases. Performers donate their time, playing across multiple local stages—inviting audiences to stroll through Leesburg’s vibrant music scene. It’s a unique blend of original songwriting, community engagement, and philanthropic impact.
September 19, 2025: Headlined by platinum-selling Southern rockers Sister Hazel at Tally Ho Theater. Doors open at 6 PM, with music starting at 7 PM.
September 20, 2025: A special “Songs and Stories from the Crossroads” evening featuring Andy Summers—legendary guitarist from The Police—performed live with an on-stage interview. Doors open at 7 PM; performance begins at 8 PM.
Daytime Showcase (Sept 20): Over 30 musicians and bands deliver 60-minute sets at various downtown venues from 3 PM to 8:30 PM—open to the public with no ticket required.
Proceeds from the festival benefit nine local nonprofit organizations—including The Arc of Loudoun, Dulles South Food Pantry & Soup Kitchen, Food for Neighbors, and others focused on supporting children in need. Through the power of live music, community venues, and giving artists, Crossroads Music Festival creates connection, raises funds, and amplifies local creativity.
Saturday music showcases 3-8:30pm
Experience over 30 music showcases at multiple locations in Historic Downtown Leesburg, VA
(No TICKETS required for Saturday Music Showcase performances)
Saturday Music Showcases including: