| Raccoon Creek Bluegrass Festival | Dallas | GA | United States | July | Bluegrass |
| Rainier Pickin’ Party | Rainier | WA | United States | August | Bluegrass |
| RapidGrass Bluegrass Festival | Idaho Springs | CO | United States | August | Bluegrass |
| Re/Evolution Festival | Darrington | WA | United States | August | Bluegrass, Jam |
| Rebels & Renegades Festival | Monterey | CA | United States | October | Folk, Jam, Country |
| Red Ants Pants Festival | White Sulphur Springs | MT | United States | July | Bluegrass, Rock |
| Red Lodge Songwriter Festival | Billings | MT | United States | June | Singer-songwriter, Americana, folk, and roots music |
| Red River Songs | Red River | NM | United States | February | Bluegrass |
| Red Wing Roots Music Festival | Mt. Solon | VA | United States | June | Bluegrass |
| Redwest Festival | Salt Lake City | UT | United States | October | Country |
| Redwood Ramble | Navarro | CA | United States | July | Bluegrass |
| Reevestock | Elkin | NC | United States | October | Folk, Jam |
| Reggae on the Mountain | Topanga | CA | United States | August | Reggae |
| Reggae on the River | Humboldt County | CA | United States | August | Reggae |
| Reggae On The Way | Tacoma | WA | United States | July | Reggae |
| Reggae Rise Up | St. Petersburg | FL | United States | March | Reggae |
| Reggae Rise Up Vegas | Las Vegas | NV | United States | October | Reggae |
| Rehoboth Beach Jazz Festival | Rehoboth Beach | DE | United States | October | Jazz, with a focus on smooth jazz and R&B |
| Remington Ryde Bluegrass Festival | Centre Hall | PA | United States | June | Bluegrass |
| Rhode Island Folk Festival | East Providence | RI | United States | August | Folk, with strong representation of Americana, singer-songwriter, and roots music. This free festival focuses on showcasing local and regional talent. |
| Rhythm and Roots | Charlestown | RI | United States | September | Americana, Bluegrass, Folk |
| Rhythms on the Rio | Del Norte | CO | United States | August | Americana, Bluegrass |
| Richmond Bluegrass Jam | Richmond | VA | United States | May | Bluegrass |
| Richmond East Moose Lodge Apple, Cider, Bluegrass Festival | Ashland | VA | United States | September | Bluegrass |
| Riot Fest Chicago | Chicago | IL | United States | September | Alternative, EMO, Hip Hop, Metal, Punk, Rock |
| River Falls Roots & Bluegrass Music Festival | River Falls | WI | United States | April | Bluegrass |
| River Song Festival | Hutchinson | MN | United States | July | Folk, Americana, Blues, Bluegrass, Rock |
| Riverfront Revival | Charleston | SC | United States | October | Bluegrass, Country, Jam |
| Rock The Dock | Lake George | NY | United States | July | Jam |
| Rock the Locks | Umatilla | OR | United States | October | Rock, Country, Blues |
| Rock the Rind | Brownstown | IN | United States | August | Country |
| Rock the South | Cullman | AL | United States | July | Country |
| Rockbridge Mountain Music Dance Festival | Buena Vista | VA | United States | September | Bluegrass |
| Rockin’ The Rivers | Three Forks | MT | United States | August | Rock, Country, Blues |
| Rocky Mountain Folks Festival | Lyons | CO | United States | August | Folk music, with elements of Americana, singer-songwriter, and roots music. |
| RockyGrass Festival | Lyons | CO | United States | July | Bluegrass, with potential inclusion of Americana, Folk and Roots influences. |
| ROMP Fest | Owensboro | KY | United States | June | Bluegrass |
| Rooster Walk Music & Arts Festival | Martinsville | VA | United States | May | Alternative, Bluegrass, Country, Folk, Rock |
| Roostertail Music Festival | Madison | IN | United States | July | Bluegrass, Country, Rock |
| Roots & Rhythm Festival | Morris | IL | United States | September | Roots, Americana, blues, folk |
| Roscolusa Songwriter Festival | Ponte Vedra | FL | United States | July | Singer-songwriter, Country, Americana, folk |
| Rudy Fest Bluegrass Festival | Grayson | KY | United States | June | Bluegrass |
