For its third year, the Annapolis Baygrass Music Festival returns to its beachfront location at Sandy Point State Park along the Chesapeake Bay in Annapolis, Maryland, on Saturday and Sunday, September 20-21, 2025. People from all over the region and across North America celebrate in this picturesque destination while listening to the finest music rooted in progressive bluegrass, improvisational jam, and American roots music. Annapolis Baygrass will welcome fourteen bands and three artists-at-large over two days on two alternating beachside stages.

Festival goers will enjoy two days of exciting activities, which include yoga, beach and yard games, a fun kid zone, and interactive workshops with bay conservation non-profits and musicians.

Last year, we bore witness to the magical festival grounds for two incredible days.  We walked the site, played on the beach, ran into legendary musicians who perused through the vendor booths and watched in awe as living legends such as Sam Bush held a workshop event.

Annapolis Baygrass is thrilled to announce the 2025 lineup! Widely known for their dazzling live performances and incredible light shows, festival headliners Greensky Bluegrass will perform two sets. The festival is thrilled to have these seasoned road warriors from Michigan make their Baygrass debut! 

Over a beautiful fall weekend, fans will get to enjoy music from headliner Greensky Bluegrass, who will perform two sets.  The second headliner has yet to be announced, but rest assured, it will be worth the wait.

Over the weekend, Railroad Earth, Kitchen Dwellers, The Travelin' McCourys, LaMP, Kyle Hollingsworth Band, Larry Keel's Electric Larry Land, Sam Grisman Project, The Last Revel, Midnight North, Pressings Strings, and Geraldine will perform on one of the two majestic stages.  Like last year, we are sure there will be many unique collaborations between main-stage artists.  

Speaking of unique collaborations, there will be three artists-at-large, including Holly Bowling, Kyle Tuttle, and returning local legend Ron Holloway.

This year, Annapolis Baygrass Music Festival is celebrating the 60th anniversary of the Grateful Dead and their incredible influence on the jamgrass and bluegrass culture and music scene!  With this in mind, The Travelin’ McCourys will be presenting The Grateful Ball, while known Deadhead, Larry Keel, brings his simultaneously gritty and suave original music in electric format with his new project, Electric Larry Land.  Carrying the torch for the Grateful Dead's original bassist, Phil Lesh, Baygrass is excited to welcome San Francisco Bay-area band Midnight North— featuring Phil's son, Grahame Lesh.

Rounding out the family affair and Grateful Dead Family, Sam Grisman Project showcases a genuine passion and appreciation for the legacy of Sam’s father, David Grisman, and his close friend, Jerry Garcia, by playing some of the beloved “Dawg music” repertoire as well as sharing their own original music.

While listening to some of the best local and national bluegrass music, fans can dance in the sand, enjoy fresh oysters and Maryland seafood, chase it down with local craft brews and wines, and enjoy fun activities for all ages.

See you all in:

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