| Annapolis Baygrass Music Festival | Annapolis | MD | United States | September | Fall Equinox | 2 Days | All Ages | Bluegrass | Progressive bluegrass, jamgrass, and Americana |
| Charm City Bluegrass Festival | Baltimore | MD | United States | May | 1st Weekend | 2 Days | All Ages | Bluegrass | Bluegrass, Americana, folk, and acoustic music |
| Roots on the River | Chestertown | MD | United States | September | 2nd Weekend | 3 Days | All Ages | Americana & Roots | Americana, Roots, Blues, Folk, with influences of Rock and Country. |
| DelFest | Cumberland | MD | United States | May | Memorial Day Weekend | 4 Days | All Ages | Bluegrass | Bluegrass, Americana, roots music |
| Bear Legacy Bluegrass Festival | Havre de Grace | MD | United States | July | 3rd Weekend | 2 Days | All Ages | Bluegrass | Bluegrass |
| Hollywood Rescue Squad Bluegrass Festival | Leonardtown | MD | United States | Check Online | Check Online | Check Online | All Ages | Bluegrass | Bluegrass |
| Bluegrass by the Bay | Ocean City | MD | United States | Check Online | Check Online | Check Online | All Ages | Bluegrass | Bluegrass |
| Delmarva Folk Festival | Salisbury | MD | United States | May | Memorial Day Weekend | 3 Days | All Ages | Folk | Primarily Folk, with a strong representation of Americana, Singer-Songwriter, and Roots music. |
| Common Ground on the Hill: Roots Music & Arts Festival | Westminster | MD | United States | July | 2nd Weekend | 1 Day | All Ages | Bluegrass | Roots music, Americana, folk, traditional music |
| Deer Creek Fiddlers’ Convention | Westminster | MD | United States | June | 1st Weekend | 1 Day | All Ages | Bluegrass | Fiddle music, bluegrass, traditional music |