The Annapolis Baygrass Music Festival takes place September 19-20, 2026 in Annapolis, Maryland, featuring a stellar lineup of bluegrass, rock, folk, americana, and jam band performers. Headliners include legendary Southern rock band Little Feat, progressive bluegrass pioneers Yonder Mountain String Band, and banjo virtuoso Béla Fleck alongside his My Bluegrass Heart project. The festival showcases 15 artists total, with additional notable acts including mandolin master Sam Bush, Celtic rock band Scythian, all-female bluegrass supergroup Sister Sadie, and emerging talents like Fireside Collective and Midnight North. This two-day event offers fans a diverse mix of traditional and contemporary roots music from established legends and rising stars in the americana scene.