Annapolis Baygrass Festival 2025 Recap: Building Community & Breaking Boundaries

For some music festivals, particularly those built around a specific genre, the festival’s name is of critical importance, giving attendees a sense for what they can expect.

The Annapolis Baygrass Music Festival, then, might conjure images of fans and artists alike by the edge of the Chesapeake Bay, picking and dancing to classic bluegrass songs performed on traditional acoustic instruments. But to adapt a key theme from the Great Bard’s tragedy, Romeo and Juliet, names don’t always tell the full story; and last weekend, the third annual Baygrass Fest showed that there’s more to it than its name might suggest at first glance.

More Than Music: A Mission in Action Set Down by the Bay

Set against the awe-inspiring backdrop of the Chesapeake Bay, Baygrass kicked off on a warm September 20 in Sandy Point State Park.

“It was incredible to play while looking out over the beauty of the Bay,” said saxophonist Patrick Rainey, a newcomer to the fest and one of three artists-in-residence who sat-in with many of the headline performers over the course of the weekend.

John Bolten three-time Baygrass performer and writer of the festival’s theme, “In the Water,” echoed the sentiment: “It never gets old.” (Bolten’s professional background is in hydrology, and his band, Geraldine, anticipates releasing their next LP in 2026.)

Perhaps that’s the first clue that this isn’t just a bluegrass festival that happens to be by the bay; it’s a baygrass festival, a holistic experience where the tidal rhythms of the location infuse the music, encouraging it to stretch beyond its comfortable boundaries.

Baygrass founders — Ron Peremel, John Way, and Ron Katz — stand by the festival’s motto – Every Jam Saves the Bay and Helps a Mind – as they pursue its dual social mission of Chesapeake Bay preservation and mental health education and support. This sometimes means making decisions that challenge festival economics, both for the promoters and vendors; but the proof is in the pudding.

Greening Director Walter Wright, who advocates eco friendly practices at festivals and everyday life, led a volunteer team of “compost cowboys” helped divert over 50 cubic yards of waste from the landfill, while the BayGuardian Village hosted passionate non-profits.

According to Dr. Olivia Caretti, the Oyster Recovery Partnership, one of the beneficiaries of Baygrass’ profits, has added an incredible 14 billion oysters to the bay over the last 30 years. Bolten also cited the Citizen Science booth as being somewhere attendees can learn specific ways they can support Bay conservation. Read more about the festival’s environmental impact here.

A Sense of Community

The festival’s dual mission manifests in other ways as well, with local partnerships resulting in custom festival brews like Dewey Beer Company’s Bay Keeper IPA and Pickett Brewing’s Way Back Home Hazy IPA, a collaboration with longtime home brewer and first-time festival performer Kyle Hollingsworth, of The String Cheese Incident.

“Brewing is a lot like making a song or a record: you have the recipe, you have the ingredients, and you’re not sure how it’s going to turn out,” Hollingsworth said.

With a new album on the way in Spring 2026, Hollingsworth embraces the risk and surprise that exist both in brewing and in music. As he put it, “Sometimes I’ll make the best beer I’ve ever made, or the worst solo I’ve ever taken.” Either way, the exercise in creativity fosters further community building.

That same sense of community pervaded the festival’s wellness initiatives. The VA Way Sober Safe Space provided a crucial sanctuary, while attendees punctuated their day with beach yoga set to live music from one of the two festival stages. It all contributes to an atmosphere that Jason Law, of media company Festy GoNuts, described perfectly.

“Baygrassers are like family and treat each other with love and kindness,” Law said.

This is palpable in every aspect of the festival, including the presence of legendary songwriter Burle Galloway, who has worked with most of the bands at the festival but showed up not to perform but rather to tend bar, as he has for years in Telluride. All of this amounts to both fans’ and performers’ desire to make the festival an annual tradition.

“Baygrass is quickly turning into one of our all time favorite festivals,” said Max Davies, guitarist of the Baygrass veterans Kitchen Dwellers.

Tradition Meets Evolution

As the Baygrass team seeks to move the bar for greenness at festivals, they’re also quietly redefining what a bluegrass festival can be, demonstrating that its identity is forged not in stylistic purity, but in a shared ethos of musical exploration and radical inclusivity. The festival’s lineup offered a fascinating study in tradition and authenticity, modernity and originality, both in terms of the artists who appeared, as well as their song choices and collaborations.

The lineup included some of the top names in traditional bluegrass like Railroad Earth and The Travelin’ McCourys, as well as modern boundary pushers Kitchen Dwellers, Molly Tuttle, and Greensky Bluegrass.

It also included decidedly non-bluegrass bands, including Americana artist Elliott Peck, of Midnight North; jazz-jam trio LaMP; and local rising stars, Pressing Strings, whose singer and guitarist Jordan Sokel appreciated the opportunity to push the stylistic boundaries of the Baygrass artist roster. Pressing Strings will perform a series of shows with Kitchen Dwellers in November. Likewise, Peck was humbled to be a part of the bridge between bluegrass and alt country rock.

At least one of the festival’s artists in residence – Rainey, Holly Bowling, and/or Kyle Tuttle – played (or at least sat in) during almost every set of the weekend. Tuttle, who also hosted a banjo workshop during the day, brought a traditional element to many of his sit-ins, while other collaborations defied the genre entirely: moments of Holly Bowling’s sets with GSB called to mind everything from Grateful Dead to Keith Jarrett. Both Bowling and Hollingsworth incorporated a Hammond organ and Leslie speaker into their rigs, lending an organic warmth not typically present in traditional bluegrass.

Cover songs provided another lens through which Baygrass shows its variety. The Travelin’ McCourys delivered a flawless set of traditional bluegrass, honoring the genre’s pioneers with faithful renditions of songs by Bill Monroe and John Hartford, while Sam Grisman Project opened their set with the classic Jerry Garcia-David Grisman collaboration, “Grateful Dawg.” But both bands included more modern rock tunes, including Paul Simon’s “50 Ways to Leave Your Lover” and Bruce Hornsby’s “The Way It Is,” and the McCourys also led the Grateful Ball set.)

Even further along the spectrum, bands used the bluegrass framework to interpret songs from far outside the tradition. The Last Revel delivered a rousing cover of The White Stripes’ “You Don’t Know What Love Is,” as well as a Rainey-supported cover of Modest Mouse’s “Float On” that brought at least one attendee to tears.

Guitarist Molly Tuttle, known for honoring bluegrass while stretching its boundaries, delighted the crowd with an analog version of Icona Pop’s electro-pop hit “I Don’t Care, I Love It,” as well as The Rolling Stones’ “She’s a Rainbow.”

Montana’s Kitchen Dwellers, who project traditional bluegrass and folk through a kaleidoscope of musical traditions, leaned into the bayside vibe with a spirited cover of Jimmy Buffett’s “Son of a Son of a Sailor,” while Kyle Hollingsworth Band treated the crowd to covers of tunes by Kansas and Aerosmith, as well as originals that followed chord progressions found more commonly in Phish’s music than traditional bluegrass.

These moments posed a thrilling question: what constitutes an authentic bluegrass performance? Is it the song’s origin, or the instruments and conviction with which it’s played?

Originality & Authenticity

With its lineup and musical philosophy, Baygrass walks a fine line that highlights what Reed Mathis describes as the hope and fear of the new, in The Gifts of Improvising, his excellent podcast from Osiris Media. It’s no coincidence that two of the weekend’s key figures, Holly Bowling and Elliott Peck, both have been guests on Mathis’ pod, Peck herself performing on a set of tunes currently available on streaming platforms; their presence at Baygrass felt like a real-world extension of the discussion.

Nowhere was “the hope in the new” more palpable than during Holly Bowling’s sit-in with Greensky Bluegrass. Bowling, a solo pianist who blends classically trained virtuosity with emotional immersion, helped elevate the band’s improvisation into something truly transcendent.

Bowling’s philosophy perfectly captured the festival’s spirit, appreciating that a few minutes into some of their jams, it’s impossible to tell what song gave rise to the jam: it was a beautiful thing to see her and Greensky achieve that state of pure, in-the-moment invention.

Of course, some bands pushed boundaries by existing outside of them entirely, like the improvisational jazz-funk of LaMP or Larry Keel‘s Electric Larry Land, a project that presents his gritty original music in an electric format, creating an irresistible sonic groove.

The Baygrass Identity

So, is “Baygrass” a misnomer?

After a weekend soaking in its sounds and spirit, the answer is a resounding no. If anything, Baygrass is becoming a genre unto itself, where boundary lines are joyfully erased: between artist and audience, between musical styles, between a good time and a good cause.

By refusing to be constrained by a single genre, the organizers have built something more durable: a community. Baygrass has found its identity not in a rigid definition, but in the beautiful, boundary-breaking spaces where a thriving community comes to celebrate the thrilling hope of the new.

To see is to believe: mark your calendars for September 19 and 20, 2026.