| Annapolis Songwriters Festival | Annapolis | MD | United States | September | 2nd Weekend | 4 Days | Americana, Bluegrass, Country, Folk, Indie, Rock | Music |
| Annapolis Baygrass Music Festival | Annapolis | MD | United States | September | Fall Equinox | 2 Days | Progressive bluegrass, jamgrass, and Americana | Music |
| Charm City Bluegrass Festival | Baltimore | MD | United States | May | 1st Weekend | 2 Days | Bluegrass, Americana, folk, and acoustic music | Music |
| Harmony Woods Music & Beer Fest | Bel Air | MD | United States | June | 3rd Weekend | 2 Days | Bluegrass | Music |
| Berlin Fiddlers Convention | Berlin | MD | United States | September | 3rd Weekend | 3 Days | Bluegrass | Music |
| Sultana Downrigging Tall Ship and Bluegrass Festival | Chestertown | MD | United States | November | 1st Weekend | 3 Days | Bluegrass | Music |
| Roots on the River | Chestertown | MD | United States | September | 2nd Weekend | 3 Days | Americana, Roots, Blues, Folk, with influences of Rock and Country. | Music |
| Hot August Music Festival | Cockeysville | MD | United States | August | 2nd Weekend | 1 Day | Bluegrass, Jam | Music |
| All Things Go Festival | Columbia | MD | United States | September | 4th Weekend | 2 Days | Indie, Pop, Rock | Music |
| Crisfield Bluegrass and Sunset Festival | Crisfield | MD | United States | June | 3rd Weekend | 1 Day | Bluegrass | Music |
| DelFest | Cumberland | MD | United States | May | Memorial Day Weekend | 4 Days | Bluegrass, Americana, Roots, Jam, Rock | Music |
| The Ramble Festival | Darlington | MD | United States | October | 2nd Weekend | 3 Days | Bluegrass | Music |
| Bear Legacy Bluegrass Festival | Havre de Grace | MD | United States | July | 3rd Weekend | 2 Days | Bluegrass | Music |
| Hollywood Rescue Squad Bluegrass Festival | Leonardtown | MD | United States | September | 2nd Weekend | 3 Days | Bluegrass | Music |
| Country Calling | Ocean City | MD | United States | October | 1st Weekend | 2 Days | Country | Music |
| Oceans Calling Festival | Ocean City | MD | United States | September | 4th Weekend | 3 Days | Indie, Pop, Rock | Music |
| Bluegrass by the Bay | Ocean City | MD | United States | September | Last Weekend | 3 Days | Bluegrass | Music |
| Lone Cedar Acres Bluegrass Festival | Pittsville | MD | United States | October | 4th Saturday | 1 Day | Bluegrass | Music |
| Delmarva Folk Festival | Salisbury | MD | United States | May | Memorial Day Weekend | 3 Days | Folk, with a strong representation of Americana, Singer-Songwriter, and Roots music. | Music |
| Upperco Music Festival | Upperco | MD | United States | September | 3rd Weekend | 5 Days | Bluegrass | Music |
| Common Ground on the Hill Roots Music & Arts Festival | Westminster | MD | United States | July | 2nd Weekend | 1 Day | Roots music, Americana, folk, traditional music | Music |
| Deer Creek Fiddlers’ Convention | Westminster | MD | United States | June | 1st Sunday | 1 Day | Fiddle music, bluegrass, traditional music | Music |
