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. People from all over the region and across North America celebrate in this picturesque destination while listening to the finest progressive bluegrass, improvisational jam, and American roots music. Annapolis Baygrass will welcome 14 bands and three artists-at-large over two days on two alternating beachside stages.
Annapolis Baygrass is thrilled to announce Molly Tuttle as the surprise headliner! Molly has recently announced her new album and band, and Baygrass is honored to be among their first stops on the accompanying tour as they dazzle the crowd with a hybrid of pop, country, rock, and flat-picking. She will be joining a stellar festival lineup that includes a blend of regional and national acts and was announced earlier this year.
Annapolis Baygrass is also pleased to announce the addition of Baltimore’s Patrick Rainey to the 2025 Baygrass lineup as Artist-at-Large! Known for his soulful sax stylings and his time with The Bridge, Patrick lights up the stage with his passion and energy. Get ready for spontaneous sit-ins, soaring solos, and serious sax magic all weekend long. Baygrass is sending love to Ron Holloway, who will not be able to return to the festival this year due to personal reasons. Patrick will be joining forces with Holly Bowling on keys/piano and Kyle Tuttle on banjo—with all three performing both days of the festival.
Annapolis Baygrass is excited to announce the daily lineups! Single day tickets are on sale now, with a price increase on Tuesday, June 24.
Saturday headliners, Greensky Bluegrass, are widely known for their incredible live performances and light shows and will perform two sets in their Baygrass debut. Also on Saturday, the Kitchen Dwellers will return for a consecutive year with their mind-bending, folk-infused, psychedelic rock Galaxy Grass.
Others performing on Saturday include LaMP, featuring Russ Lawton (of Trey Anastasio Band), Scott Metzger (of Joe Russo’s Almost Dead), and Ray Paczkowski (of Trey Anastasio Band); Larry Keel’s Electric Larry Land; Sam Grisman Project; 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; and Annapolis Baygrass House Band: Geraldine, a high-energy, country-leaning string band, who is returning for a third year.
Molly Tuttle is the Sunday headliner, along with longtime mainstay in the festival scene, Railroad Earth, who is returning 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!”
The Sunday lineup also includes The Travelin' McCourys with their crisp and innovative bluegrass, as well as The Travelin’ McCourys presenting The Grateful Ball; Kyle Hollingsworth (keyboardist for the String Cheese Incident) and his band, who perform in a mosaic of styles, from rock to classical, ragtime to bebop; Minnesota-based The Last Revel with their 4-part harmonies and impassioned bluegrass performances; and the upbeat and imaginative Annapolis-based trio, Pressing Strings.
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!"
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.
The Washington Post wrote “For fans of bluegrass and Americana, it doesn’t get much better than the Baygrass Festival…The setting, at Sandy Point State Park, offers gorgeous views of the Chesapeake Bay. There’s yoga on the sand, as well as swimming; workshops… a space with games and crafts for kids; beach games and bars; and food vendors offering crab cakes and wood-fired pizzas.”
"Baygrass is more than a music festival," says Ron Peremel, CEO/Founder. "In 2024, with attendees from 37 states and Canada, that concept really came to life in a big way. The music connected people with our mission. A portion of every dollar spent on tickets, beverages, and merchandise supports our nonprofit partners—Watershed Stewards Academy, Oyster Recovery Partnership, and Alliance for the Chesapeake Bay—and raised over $32,000 for Bay conservation in 2024. This is what we mean by ‘Every Jam Saves the Bay.’"
Baygrass offers an elevated culinary experience featuring fresh seafood, gourmet BBQ, wood-fired pizzas, delicious vegan and vegetarian delicacies, and other locally curated culinary options. Attendees will enjoy a regional collaboration of tasty microbrews, fresh craft cocktails, fine wines, and hard-craft seltzers, as well as delicious non-alcoholic beer and mocktails.
There will be activities for all ages, including beachfront yoga, beach and yard games, a spectacular KidZone, a craft vendor village, and more. Baygrass artists and non-profit partners will host interactive workshops at the Workshop Pavilion and Bay Guardian Village focused on music, mental wellness, and Bay conservation. With a strong commitment to sustainability, Baygrass has become one of the nation’s leading eco-focused festivals.
Read more about the Annapolis Baygrass mission and history in these in-depth interviews with Permel by Live for Live Music and in environmental magazine, One Beautiful Planet.
“Remind oneself that amidst the complexities of life, embracing moments of joy isn't just about indulgence—it's about nurturing our mental health. We can tap into a boundless well of joy through the universal language of music—because "Every Jam Helps a Mind," says Baygrass co-founder/chief operations officer, John Way—an Army veteran and mental health first aid instructor.
John is the founder of The VA Way and has partnered with Baygrass to bring together key mental health and well-being resources to the festival, including the Anne Arundel County Department of Health, the National Alliance on Mental Illness, the National Council for Mental Wellbeing, GrooveSafe, and the Call 988 initiative. The VA Way sponsors a sober space at the festival, emphasizing its commitment to a culture of mindfulness and sobriety.
Sandy Point State Park, a 786-acre Maryland State Park located along the northwestern shore of Chesapeake Bay, provides a perfect backdrop for this one-of-a-kind festival. With stunning views and ample space, festival-goers can spread out and enjoy themselves in comfort and style on the sandy beaches. The site is ADA accessible.
Annapolis Baygrass offers several local lodging partners and camping options nearby. These discounted options are on a first-come, first-served basis and fit all budgets. Shuttle service will make the stay even easier, with shuttle passes serving many of the lodging locations.
Annapolis Baygrass Music Festival 2025
Greensky Bluegrass (2 sets)
Molly Tuttle
Railroad Earth
The Travelin’ McCourys
Kitchen Dwellers
LaMP (Russ Lawton, Scott Metzger, Ray Paczkowski)
The Grateful Ball featuring The Travelin’ McCourys
Kyle Hollingsworth Band
Larry Keel’s Electric Larry Land
Sam Grisman Project
The Last Revel
Midnight North
Pressing Strings
Geraldine
Artists-at-Large:
Holly Bowling
Kyle Tuttle
Patrick Rainey
Learn more about the Annapolis Baygrass mission, green practices, VIP options, lodging and shuttles, and sign up to be a volunteer at www.baygrassfestival.com.
