For its third year, 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. Annapolis Baygrass will welcome 14 bands and three artists-at-large over two days on two alternating beachside stages.
Annapolis Baygrass has announced its 2025 lineup. Festival headliners Greensky Bluegrass will perform two sets. Th
Railroad Earth, a longtime mainstay in the festival scene known for their eloquent songcraft, bluegrass soul, and rock ‘n’ roll spirit—returns to Annapolis Baygrass after headlining in 2023. Tim Carbone says, “Railroad Earth is really looking forward to coming back to the Annapolis Baygrass Music Festival this September! We had such a great time last go-around. The festival grounds are beautiful, right alongside the bay, and the lineup is eclectic and strong!”
Travel to the outer edges of bluegrass with the Kitchen Dwellers, who are returning for a consecutive year with their mind bending, folk-infused psychedelic rock energy. The Travelin’ McCourys‘ crisp and innovative music will undoubtedly provide an exceptional bluegrass experience.
LaMP, featuring Russ Lawton (of Trey Anastasio Band), Scott Metzger (of Joe Russo’s Almost Dead), and Ray Paczkowski (of Trey Anastasio Band), is a musical force to be reckoned with! The melodic and harmonic interplay between Paczkowski’s swirling organ and clavinet dancing with Metzger’s acrobatic melodies on telecaster, driven by Lawton’s unflappable backbeat, comes together with alchemical synthesis to create a fresh, so-tight-it’s-free sound, permeated with technical prowess and a deep-pocket punch.
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! Embracing that spirit, the 2025 Annapolis Baygrass artwork, created by Liz Burr Design, bursts with vibrant sense and color, capturing the festival’s vibe with the musical terrapins and crab, glowing bioluminescence, and the night sky shining brightly—in the shadow of the brand new crescent moon.
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 on the common thread of the Dead’s music, Baygrass is excited to welcome San Francisco Bay-area band Midnight North—featuring harmonies by Grahame Lesh and Elliott Peck along with bassist Connor O’Sullivan and drummer/banjo player Nathan Graham. Their original music carries on the light from their forefathers. “It’s a generational thing… It’s about what’s passed down to us and what we pass on. The songs and the community are the pillars holding this up,” says Lesh, who has toured with his father as a member of Phil Lesh’s Terrapin Family Band and Phil Lesh & Friends. “We’re so thankful to be part of this scene. This music is timeless.”
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 original music that their own collective has to offer.
Kyle Hollingsworth (keyboardist for the String Cheese Incident) and his band perform in a mosaic of styles, from rock to classical, ragtime to bebop. Hollingsworth says, “I’m super psyched to be involved in the Annapolis Baygrass this year. Growing up in Baltimore, I used to spend a lot of my time on the Chesapeake Bay, excited to support this event! What a great combination of music and community! I can’t wait to rock out with you all!”
The Last Revel brings a full spectrum of modern Americana to life with lush arrangements of four-part vocal harmonies, acoustic guitar, upright bass, fiddle, and 5-string banjo to consistently support impassioned performances of their honest and heartfelt songwriting. They have a new album on the way which was produced by Dave Simonett of Trampled by Turtles.
Pressing Strings, a critically acclaimed Annapolis-based trio, offers an upbeat, imaginative, and inspiring sound. Annapolis Baygrass House Band: Geraldine, a high-energy, country-leaning string band, returns for a third year.
Artists-at-Large include Holly Bowling on keys/piano, Kyle Tuttle on banjo, and Ron Holloway returns for another year on saxophone. Holloway says, “Baygrass Music Festival [2024] was a bona fide HOOT! Everything about it, including the very attentive and friendly staff, made us feel at home… The location of the festival is absolutely beautiful! Getting to do what I love as my profession elevated the whole experience to musical nirvana for me! It was so much fun; I was expecting to get arrested at any moment!”
