Annapolis Baygrass Music Festival Unveils 2025 Lineup

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 music rooted in 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.

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!

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!" 

And if that wasn't enough, stay tuned this June for an additional “Surprise Headliner” to be announced!

“The Baygrass selection process sets a goal to foster one-of-a-kind artist collaborations, which are quickly proving to be legendary, and a unique mix of music to provide excitement for multiple demographics. Our goal is to make it as fun and unique for the artists as it is for our amazing Baygrassers,” says Thom Bloom (Director of Talent & Programming). 

Annapolis Baygrass offers 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 throughout the weekend 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.

"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 features an elevated culinary experience with 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. 

“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 for a perfect weekend. 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)

*Surprise Headliner Announced Soon!

Railroad Earth 

Kitchen Dwellers 

The Travelin’ McCourys 

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

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