| Year | Association | Category | Nominated work | Result | Ref |
| 2016 | International Bluegrass Music Awards | Momentum Award | Herself | Won | |
| 2017 | Guitar Player of the Year | Won | |
| 2018 | International Folk Music Awards | Song of the Year | "You Didn't Call My Name" | Won | |
| Americana Music Honors & Awards | Instrumentalist of the Year | Herself | Won | |
| International Bluegrass Music Awards | Emerging Artist of the Year | Nominated | |
| Guitar Player of the Year | Won |
| Female Vocalist of the Year | Nominated |
| Album of the Year | Rise | Nominated |
| Song of the Year | "You Didn't Call My Name" | Nominated |
| Recorded Event of the Year | "Swept Away"[A] | Won |
| 2019 | International Bluegrass Music Awards | Female Vocalist of the Year | Herself | Nominated | |
| Guitar Player of the Year | Nominated |
| Song of the Year | "Take the Journey"[B] | Nominated |
| Collaborative Recording Of The Year | "Soldiers Joy/Ragtime Annie"[C] | Nominated |
| 2020 | International Bluegrass Music Awards | Female Vocalist of the Year | Herself | Nominated | |
| Guitar Player of the Year | Nominated |
| 2021 | International Bluegrass Music Awards | Female Vocalist of the Year | Herself | Nominated | |
| Guitar Player of the Year | Nominated |
| 2022 | International Bluegrass Music Awards | Entertainer of the Year | Molly Tuttle & Golden Highway | Nominated | |
| Instrumental Group of the Year | Nominated |
| Female Vocalist of the Year | Herself | Won |
| Guitar Player of the Year | Nominated |
| Album of the Year | Crooked Tree | Nominated |
| 2023 | Grammy Awards | Best New Artist | Herself | Nominated | |
| Best Bluegrass Album | Crooked Tree | Won |
| International Folk Music Awards | Album of the Year | Won | |
| International Bluegrass Music Awards | Entertainer of the Year | Molly Tuttle & Golden Highway | Nominated | |
| Instrumental Group of the Year | Nominated |
| Song of the Year | "Crooked Tree" | Won |
| Album of the Year | Crooked Tree | Won |
| Collaborative Recording of the Year | "From My Mountain (Calling You)"[D] | Nominated |
| Female Vocalist of the Year | Herself | Won |
| Guitar Player of the Year | Nominated |
| 2024 | Grammy Awards | Best Bluegrass Album | City of Gold | Won | |
| 2026 | Grammy Awards | Best Americana Album | So Long Little Miss Sunshine | Pending | |
| Best Americana Performance | "That's Gonna Leave a Mark" | Pending |