| Bridgetown Bluegrass & Folk Festival | Portland | OR | United States | May | 1st Saturday | 1 Day | Bluegrass and Folk | Music |
| Long Beach Bluegrass Festival | Long Beach | CA | United States | May | 1st Saturday | 1 Day | Bluegrass | Music |
| Birdfest | Pinewood | SC | United States | May | 1st Weekend | 2 Days | Bluegrass | Music |
| Bluegrass at the Junction | Nashville | NC | United States | May | 1st Weekend | 1 Day | Bluegrass | Music |
| Boxcar Pinion Bluegrass Festival | Chickamauga | GA | United States | May | 1st Weekend | 3 Days | Bluegrass | Music |
| Charm City Bluegrass Festival | Baltimore | MD | United States | May | 1st Weekend | 2 Days | Bluegrass, Americana, folk, and acoustic music | Music |
| Gallagher Fest | Murfreesboro | TN | United States | May | 1st Weekend | 1 Day | Bluegrass | Music |
| Key West Songwriter Festival | Key West | FL | United States | May | 1st Weekend | 5 Days | Singer-songwriter, Americana, folk | Music |
| Little Roy & Lizzy Music Festival | Lincolnton | GA | United States | May | 1st Weekend | 3 Days | Bluegrass | Music |
| Lone Star Smokeout | Arlington | TX | United States | May | 1st Weekend | 3 Days | Country | Music |
| Mr. B’s Bluegrass Festival | Woodford | VA | United States | May | 1st Weekend | 3 Days | Bluegrass | Music |
| Palm Coast Songwriting Festival | Palm Coast | FL | United States | May | 1st Weekend | 4 Days | Singer-songwriter, Americana, folk | Music |
| Richmond Bluegrass Jam | Richmond | VA | United States | May | 1st Weekend | 1 Day | Bluegrass | Music |
| TheBigWonderful BEERFEST | Denver | CO | United States | May | 1st Weekend | 1 Day | Varied, often featuring local and regional bands, with a focus on the craft beer experience | Music |
| Twin Oaks Spring Bluegrass Festival | Hoboken | GA | United States | May | 1st Weekend | 3 Days | Bluegrass | Music |
| Bluegrass & Brews | Richmond | VA | United States | May | 2nd Weekend | 2 Days | Bluegrass | Music |
| Calico Bluegrass Festival | Yermo | CA | United States | May | 2nd Weekend | 2 Days | Bluegrass | Music |
| Chet Kingery Memorial Bluegrass Festival | Shelbyville | IL | United States | May | 2nd Weekend | 2 Days | Bluegrass | Music |
| Minnesota Music Festival | Minneapolis | MN | United States | May | 2nd Weekend | 2 Days | Various genres | Music |
| North Bend State Park Bluegrass Festival | Harrisville | WV | United States | May | 2nd Weekend | 2 Days | Bluegrass | Music |
| Old Settler’s Music Festival | Dale | TX | United States | May | 2nd Weekend | 4 Days | Bluegrass | Music |
| Reinhardt Bluegrass Festival | Waleska | GA | United States | May | 2nd Weekend | 2 Days | Bluegrass, with some events featuring Newgrass and Americana influences | Music |
| The Malpass Brothers Bluegrass & Country Music Festival | Denton | NC | United States | May | 2nd Weekend | 3 Days | Bluegrass | Music |
| NJ BOTMA Indoor Festival | Little Silver | NJ | United States | May | 3rd Sunday | 1 Day | Bluegrass | Music |
| Topanga Banjo-Fiddle Contest & Folk Festival | Agoura Hills | CA | United States | May | 3rd Sunday | 1 Day | Folk music, with a focus on banjo and fiddle playing, including competitions and performances | Music |
| Bloomin’ BBQ & Bluegrass | Sevierville | TN | United States | May | 3rd Weekend | 2 Days | Bluegrass | Music |
| Bluegrass BBQ Fest | Lexington | KY | United States | May | 3rd Weekend | 2 Days | Bluegrass | Music |
| Brookdale Bluegrass Spring Festival | Tres Pinos | CA | United States | May | 3rd Weekend | 1 Day | Bluegrass | Music |
| Cosmic Songwriters Festival – The Orbit Room | Bloomington | IN | United States | May | 3rd Weekend | 4 Days | Singer-songwriter, Americana, folk, with a focus on intimate performances and artist interaction | Music |
| EDC Las Vegas | Las Vegas | NV | United States | May | 3rd Weekend | 3 Days | Bass, Electronic, House, Techno | Music |
| Ellijay Songwriters Festival | Glimore County | GA | United States | May | 3rd Weekend | 11 Days | Songwriting | Music |
| Fall Strawberry Music Festival | Tuolumne | CA | United States | May | 3rd Weekend | 6 Days | Bluegrass | Music |
| FreshGrass Music Festival | Bentonville | AR | United States | May | 3rd Weekend | 2 Days | Roots, Bluegrass, Folk | Music |
| Gettysburg Bluegrass Festival | Gettysburg | PA | United States | May | 3rd Weekend | 4 Days | Bluegrass | Music |
| Greenbelt Music Festival | Clive | IA | United States | May | 3rd Weekend | 2 Days | Bluegrass | Music |
| Grottoes Bluegrass Festival | Grottoes | VA | United States | May | 3rd Weekend | 3 Days | Bluegrass | Music |
| Mosswood Meltdown | Oakland | CA | United States | May | 3rd Weekend | 2 Days | Indie | Music |
| Pickin’ by the Lake | Roxboro | NC | United States | May | 3rd Weekend | 1 Day | Bluegrass | Music |
| Steve Sutton Fest | Black Mountain | NC | United States | May | 3rd Weekend | 1 Day | Bluegrass | Music |
| Armuchee Memorial Day Bluegrass Festival | Armuchee | GA | United States | May | 4th Weekend | 3 Days | Bluegrass | Music |
| Bottlerock Napa Valley | Napa | CA | United States | May | 4th Weekend | 3 Days | Alternative, Americana, Hip Hop, Latin, Pop, R&B, Reggae, Rock | Music |
| Dr. Ralph Stanley Hills of Home Festival | McClure | VA | United States | May | 4th Weekend | 4 Days | Bluegrass | Music |
| Gathering In The Gap | Big Stone Gap | VA | United States | May | 4th Weekend | 1 Day | Bluegrass | Music |
| Patriotic Festival | Norfolk | VA | United States | May | 4th Weekend | 3 Days | Country | Music |
| Rooster Walk | Axton | VA | United States | May | 4th Weekend | 4 Days | Alternative, Bluegrass, Country, Folk, Rock | Music |
| Salmon Lake Park Bluegrass ‘Classic Fun Pick’ Weekend | Grapeland | TX | United States | May | 4th Weekend | 3 Days | Bluegrass | Music |
| Strawberry Music Festival | Grass Valley | CA | United States | May | 4th Weekend | 4 Days | Americana, folk, bluegrass, and roots music | Music |
| ArborFest Gospel Bluegrass Festival | Midland | NC | United States | May | Check Online | 1 Day | Bluegrass | Music |
| Brown County Roots Festival | Nashville | IN | United States | May | Check Online | 3 Days | Americana, roots, bluegrass, folk, with a diverse lineup across various genres | Music |
| Dollywood Barbeque & Bluegrass Festival | Pigeon Forge | TN | United States | May | Last Weekend | 3 Days | Bluegrass | Music |
| Gulf Coast Jam | Panama City Beach | FL | United States | May | Last Weekend | 4 Days | Country | Music |
| Hawaii Songwriting Festival | Kauai | HI | United States | May | Last Weekend | 3 Days | Singer-songwriter, Americana, folk | Music |
| South Carolina State Bluegrass Festival | Myrtle Beach | SC | United States | May | Last Weekend | 3 Days | Bluegrass | Music |
| White Oak Shores Spring Bluegrass Festival | Stella | NC | United States | May | Last Weekend | 3 Days | Bluegrass | Music |
| Back 40 Bluegrass Festival | Curryville | MO | United States | May | Memorial Day Weekend | 4 Days | Bluegrass | Music |
| Bearsville Bluegrass Festival | Woodstock | NY | United States | May | Memorial Day Weekend | 1 Day | Bluegrass | Music |
| Bluegrass on the Arkansas | Salida | CO | United States | May | Memorial Day Weekend | 2 Days | Bluegrass | Music |
| Carolina Hills Fiddle Fest | Union Grove | NC | United States | May | Memorial Day Weekend | 4 Days | Bluegrass | Music |
| DelFest | Cumberland | MD | United States | May | Memorial Day Weekend | 4 Days | Bluegrass, Americana, Roots, Jam, Rock | 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 |
| Floyd & Fannie Salmon Memorial Day Gospel Bluegrass Festival | Grapeland | TX | United States | May | Memorial Day Weekend | 3 Days | Bluegrass | Music |
| MeadowGrass Music Festival | Colorado Springs | CO | United States | May | Memorial Day Weekend | 3 Days | Bluegrass | Music |
| Northwest Folklife Festival | Seattle | WA | United States | May | Memorial Day Weekend | 3 Days | Folk, with strong representation of Americana, singer-songwriter, and roots music, showcasing a diverse range of artists within the folk genre. | Music |
| Pickin’ in the Rockies | Loma | CO | United States | May | Memorial Day Weekend | 1 Day | Bluegrass | Music |
| Rooster Walk Music & Arts Festival | Martinsville | VA | United States | May | Memorial Day Weekend | 4 Days | Bluegrass | Music |
| Shirner Bluegrass Festival | Timonium | CO | United States | May | Memorial Day Weekend | 1 Day | Bluegrass | Music |
| SpringFree Bluegrass Festival | Vail Village | CO | United States | May | Memorial Day Weekend | 3 Days | Bluegrass | Music |
| The Tony Rice Memorial Day MusicFest at Camp Springs | Elon | NC | United States | May | Memorial Day Weekend | 3 Days | Bluegrass | Music |
| Uncle Boojie’s Roots Revue | Louisville | KY | United States | May | Memorial Day Weekend | 2 Days | Bluegrass | Music |
| Parkfield Bluegrass Festival | Parkfield | CA | United States | May | Mother’s Day Weekend | 4 Days | Bluegrass | Music |
| Pickin’ in the Park | Pleasant Garden | NC | United States | May | WEEKEND | 1 Day | Bluegrass | Music |
