| Annapolis Songwriters Festival | Annapolis | MD | United States | September | Singer-Songwriter, Americana, Bluegrass, Country, Folk, Indie, Rock |
| Annapolis Baygrass Music Festival | Annapolis | MD | United States | September | Americana, Bluegrass and Jamgrass |
| Charm City Bluegrass Festival | Baltimore | MD | United States | May | Bluegrass, Americana, folk, and acoustic music |
| Harmony Woods Music & Beer Fest | Bel Air | MD | United States | June | |
| Berlin Fiddlers Convention | Berlin | MD | United States | September | Bluegrass |
| Sultana Downrigging Tall Ship and Bluegrass Festival | Chestertown | MD | United States | November | Bluegrass |
| Hot August Music Festival | Cockeysville | MD | United States | August | Bluegrass, Jam |
| All Things Go Festival | Columbia | MD | United States | September | Indie, Pop, Rock |
| Crisfield Bluegrass and Sunset Festival | Crisfield | MD | United States | June | Bluegrass |
| DelFest | Cumberland | MD | United States | May | Bluegrass, Americana, Roots, Jam, Rock |
| The Ramble Festival | Darlington | MD | United States | October | Bluegrass |
| Bear Legacy Bluegrass Festival | Havre de Grace | MD | United States | July | Bluegrass |
| Hollywood Rescue Squad Bluegrass Festival | Leonardtown | MD | United States | September | Bluegrass |
| Country Calling | Ocean City | MD | United States | October | Country |
| Oceans Calling Festival | Ocean City | MD | United States | September | Indie, Pop, Rock |
| Lone Cedar Acres Bluegrass Festival | Pittsville | MD | United States | October | Bluegrass |
| Delmarva Folk Festival | Salisbury | MD | United States | May | Folk, with a strong representation of Americana, Singer-Songwriter, and Roots music. |
| Upperco Music Festival | Upperco | MD | United States | September | Bluegrass |
| Deer Creek Fiddlers’ Convention | Westminster | MD | United States | May | Old-Time Fiddle music, bluegrass, traditional music |
