Annapolis Baygrass Returns to Sandy Point With Its Biggest Lineup Yet

The Annapolis Baygrass Music Festival is back at Sandy Point State Park September 19-20, 2026. This lineup is worth the drive. Little Feat headlines, joined by a bill stacked with genre heavyweights and rising names. Yonder Mountain String Band, Béla Fleck’s My Bluegrass Heart, and Sam Bush bring decades of bluegrass pedigree, while Mountain Grass Unit arrives fresh off their first-ever Grand Ole Opry appearance. TopHouse, Shadowgrass, SCYTHIAN, Sister Sadie, Fireside Collective, Midnight North, Jammy Buffet, Melody Trucks & The Fitzkee Brothers Band, and Geraldine round things out. Three artists-at-large, Allie Kral on fiddle, Alvin Lee on sacred steel guitar, and Patrick Rainey on sax, will be floating between sets all weekend, popping up in places nobody printed on the poster.

Two side-by-side stages keep things moving with barely a gap between sets. Nobody has to pick between two acts they actually want to see, more than most festivals this size can say. That format has already produced some of Baygrass’s best moments in its first three years, guest sit-ins that never showed up on any printed schedule. Cofounder John Way isn’t saying who might turn up with who this time. Given the track record, it’s worth glancing toward the stage every time somebody unfamiliar walks up.

The setting adds a lot to the atmosphere. Sandy Point is a beautiful beach, with the Bay Bridge stretched out behind the stages and the Chesapeake doing its late-summer thing, boats drifting by, a breeze coming off the water. Wander away from the stages, and there’s a whole grounds worth exploring, an artisan vendor village, beach yoga at sunset synced to whatever band is playing next door, and a Workshop Pavilion that’s become one of the better reasons to show up early.

Once again, that pavilion is worth planning around this year. Saturday brings “From Bay to Ballad,” where Burle Galloway walks the crowd through writing his song about the Chesapeake from a single drop of glacial melt to the estuary it is now, joined by Dave Johnston of Yonder Mountain String Band, Allie Kral, and Geraldine’s Cory Chubb building the arrangement live. Right after that, Alvin “Uncle Al” Lee and George “Beanmartian” Webster trace Sacred Steel from Holiness Pentecostal churches to festival stages, part concert and part oral history. Later, Oyster Recovery Partnership runs its fan-favorite “Shuck Like a Pro” class, with Ashling Kitchen handling toppings, though space fills fast. Sunday’s panel, “Bluegrass at 80,” puts Sam Bush alongside author Tim Newby and Rolling Stone’s Garret K. Woodward, tracing the genre from Bill Monroe’s 1945 Opry debut to Billy Strings filling arenas. And Sunday afternoon, John Way sits down with Cris Jacobs for “Mental Health Matters,” a real conversation about depression, recovery, and why asking for help isn’t weakness, open to anyone navigating something hard, not just musicians or veterans.

Baygrass runs on two missions underneath all the music: protecting the Chesapeake Bay through conservation and sustainability, and supporting mental health awareness. The taglines split it the same way: “Every Jam Heals the Bay” for the environment and “Every Jam Helps a Mind” for everything else. Part of the proceeds from ticket sales support the conservation side, as do some of the programs like oyster shell recycling and water refill stations. On the mental health side, Way, a NAMI program manager who’s run peer support groups for nearly seven years, keeps a sober space at the festival, backed this year by partnerships with Serenity Sisters and Happy Coffee, plus daily sober meet-ups for anyone who wants them, along with assorted other physical and mental health options.

“You want to change your perspective, listen to new music, because we have so many memories sometimes associated with past music, and it doesn’t always lead somewhere happy,” Way said. “Music can be a trigger, so you need to create new positive triggers. Get out, get social wellness, meet new circles of friends.”

Food and drink have grown into their own draw. Local chefs turn out fresh lump crab cakes, roasted and raw oysters, gourmet BBQ, and wood-fired pizzas, with a real vegan and vegetarian lineup instead of an afterthought table. The Baytoberfest Beer Garden pours local microbrews, and there are also craft cocktails, mocktails, and wine from the regional beverage partners for anyone looking for something different.

Friday night gets its own show too. The kickoff party at Maryland Hall for the Creative Arts brings Jammy Buffet and Cumberland Honey to the venue’s newly renovated Main Theatre the night before gates open at Sandy Point.

VIP is still available at $609 for the weekend, and it hasn’t sold out yet. The two-day pass includes a dedicated village with intimate performances, chef-prepared daily meals with fresh-shucked oysters, its own bar with happy hour tastings, shaded lounge seating, dedicated beach access, and air-conditioned bathrooms; the kind of package that turns a long festival day into something a little easier on the body.

Baygrass just picked up a nomination for the IBMA Industry Award for Event of the Year, putting it up against long-running festivals in France, South Carolina, California, and Ohio, not bad for something only four years old. Production and insurance costs climb every year, and festivals with far longer track records have quietly shut down the last couple of seasons. Live music like this doesn’t keep happening on its own. It needs people showing up.

For anyone getting general admission, a 2-day GA pass runs $273, which comes out to well under $20 a set once you count everyone on the bill. Single-day GA runs $161, and kids passes start at $89 for two days. Friday’s kickoff party at Maryland Hall is its own ticket at $21.

Tickets and full details are at baygrassfestival.com.

One practical suggestion before heading out: bring cash for the park entrance gate. Credit cards work, but they take longer, and having exact change ready speeds things up for everyone waiting to enjoy the festival.

Photos by Mark Raker

Dan Rozman