| Deer Creek Fiddlers’ Convention | Westminster | MD | United States | May | Old-Time Fiddle music, bluegrass, traditional music |
| TheBigWonderful BEERFEST | Denver | CO | United States | May | Variety, often featuring local and regional bands, with a focus on the craft beer experience |
| Key West Songwriter Festival | Key West | FL | United States | May | Singer-Songwriter, Americana, folk |
| Palm Coast Songwriting Festival | Palm Coast | FL | United States | May | Singer-Songwriter, Americana, folk |
| Boxcar Pinion Bluegrass Festival | Chickamauga | GA | United States | May | Bluegrass |
| Little Roy & Lizzy Music Festival | Lincolnton | GA | United States | May | Bluegrass |
| Charm City Bluegrass Festival | Baltimore | MD | United States | May | Bluegrass, Americana, folk, and acoustic music |
| Folky Fish Festival | St. James | MO | United States | May | Bluegrass, Folk |
| Camp Springs Bluegrass Festival | Elon | NC | United States | May | Bluegrass |
| Bluegrass at the Junction | Nashville | NC | United States | May | Bluegrass |
| Adirondack Bluegrass League Annual Roundup | Galway | NY | United States | May | Bluegrass |
| Birdfest | Pinewood | SC | United States | May | Bluegrass |
| Gallagher Fest | Murfreesboro | TN | United States | May | Bluegrass |
| Lone Star Smokeout | Arlington | TX | United States | May | Country |
| Bluegrass Heritage Festival | Dallas | TX | United States | May | Bluegrass |
| Richmond Bluegrass Jam | Richmond | VA | United States | May | Bluegrass |
| Mr. B’s Bluegrass Festival | Woodford | VA | United States | May | Bluegrass |
| May on the Mountain | Henagar | AL | United States | May | Bluegrass |
| Calico Bluegrass Festival | Yermo | CA | United States | May | Bluegrass |
| Chet Kingery Memorial Bluegrass Festival | Shelbyville | IL | United States | May | Bluegrass |
| Minnesota Music Festival | Minneapolis | MN | United States | May | Variety |
| The Malpass Brothers Bluegrass & Country Music Festival | Denton | NC | United States | May | Bluegrass |
| Hills of Home Festival | McClure | VA | United States | May | Bluegrass |
| Bluegrass & Brews | Richmond | VA | United States | May | Bluegrass |
| North Bend State Park Bluegrass Festival | Harrisville | WV | United States | May | Bluegrass |
| Topanga Banjo-Fiddle Contest & Folk Festival | Agoura Hills | CA | United States | May | Folk music, with a focus on banjo and fiddle playing, including competitions and performances |
| Opelika Songwriters Festival | Opelika | AL | United States | May | Singer-Songwriter, Americana, Folk and Country |
| FreshGrass Music Festival | Bentonville | AR | United States | May | American and Roots, Bluegrass, Folk |
| Strawberry Music Festival | Tuolumne | CA | United States | May | Bluegrass |
| Country Thunder Florida | Tampa | FL | United States | May | Country |
| Ellijay Songwriters Festival | Glimore County | GA | United States | May | Singer-Songwriting |
| Greenbelt Music Festival | Clive | IA | United States | May | Bluegrass |
| Cosmic Songwriters Festival – The Orbit Room | Bloomington | IN | United States | May | Singer-Songwriter, Americana, folk, with a focus on intimate performances and artist interaction |
| Bluegrass BBQ Fest | Lexington | KY | United States | May | Bluegrass |
| SEMBA May Bluegrass Festival | Houston | MN | United States | May | Bluegrass |
| EDC Las Vegas | Las Vegas | NV | United States | May | Bass, Electronic, House, Techno |
| Gettysburg Bluegrass Festival | Gettysburg | PA | United States | May | Bluegrass |
| Kilgore Station Bluegrass Festival | Cross Plains | TN | United States | May | Bluegrass |
| Nile Mile Bluegrass Festival | Pikeville | TN | United States | May | Bluegrass |
| Grottoes Bluegrass Festival | Grottoes | VA | United States | May | Bluegrass |
| AFLO Music Festival | Purcellville | VA | United States | May | Bluegrass |
| Strawberry Music Festival | Grass Valley | CA | United States | May | Americana, folk, bluegrass, and roots music |
| Bottlerock Napa Valley | Napa | CA | United States | May | Alternative, Americana, Hip Hop, Latin, Pop, R&B, Reggae, Rock |
| Armuchee Memorial Day Bluegrass Festival | Armuchee | GA | United States | May | Bluegrass |
| Salmon Lake Park Bluegrass ‘Classic Fun Pick’ Weekend | Grapeland | TX | United States | May | Bluegrass |
| Gathering In The Gap | Big Stone Gap | VA | United States | May | Bluegrass |
| Dr. Ralph Stanley Hills of Home Festival | McClure | VA | United States | May | Bluegrass |
| Patriotic Festival | Norfolk | VA | United States | May | Country |
| Gulf Coast Jam | Panama City Beach | FL | United States | May | Country |
| Hawaii Songwriting Festival | Kauai | HI | United States | May | Singer-Songwriter, Americana, folk |
| South Carolina State Bluegrass Festival | Myrtle Beach | SC | United States | May | Bluegrass |
| Dollywood Barbeque & Bluegrass Festival | Pigeon Forge | TN | United States | May | Bluegrass |
| MeadowGrass Music Festival | Colorado Springs | CO | United States | May | Bluegrass |
| Bluegrass on the Arkansas | Salida | CO | United States | May | Bluegrass |
| SpringFree Bluegrass Festival | Vail Village | CO | United States | May | Bluegrass |
| Uncle Boojie’s Roots Revue | Louisville | KY | United States | May | Bluegrass |
| DelFest | Cumberland | MD | United States | May | Bluegrass, Americana, Roots, Jam, Rock |
| Delmarva Folk Festival | Salisbury | MD | United States | May | Folk, with a strong representation of Americana, Singer-Songwriter, and Roots music. |
| Back 40 Bluegrass Festival | Curryville | MO | United States | May | Bluegrass |
| The Tony Rice Memorial Day MusicFest at Camp Springs | Elon | NC | United States | May | Bluegrass |
| Bearsville Bluegrass Festival | Woodstock | NY | United States | May | Bluegrass |
| Floyd & Fannie Salmon Memorial Day Gospel Bluegrass Festival | Grapeland | TX | United States | May | Bluegrass |
| Rooster Walk Music & Arts Festival | Martinsville | VA | United States | May | Alternative, Bluegrass, Country, Folk, Rock |
| Northwest Folklife Festival | Seattle | WA | United States | May | Folk, with strong representation of Americana, singer-songwriter, and roots music, showcasing a diverse range of artists within the folk genre. |
| Parkfield Bluegrass Festival | Parkfield | CA | United States | May | Bluegrass |
