Article Contributed by Howard Horder
Published on 2026-09-28
Béla Fleck | Annapolis Baygrass Festival 2026 | photos by Howard Horder
The Annapolis Baygrass Music Festival has quickly become an annual must-see music event. Now in its fourth year, the festival is held beachside on the Chesapeake Bay at Sandy Point State Park in Annapolis, Maryland. The 2026 festival, held September 19 and 20, featured two full days of top-notch bluegrass, Americana and jam-band music. The bands played on two side-by-side stages, alternating between the “Baygrass Stage,” closest to the bay, and the adjacent “Every Jam Heals the Bay” stage.
The festival opened Saturday morning with Melody Trucks & The Fitzkee Brothers Band. The band features Melody Trucks on percussion and vocals, Drew Fitzkee on bass guitar and vocals, Alex Fitzkee on drums and vocals, and Will Bart on lead guitar. This band knows the Allman Brothers Band catalog backwards and forwards, and they are clearly passionate about the music. They play together as a unit, interspersing the setlist with original compositions written by Alex and Drew, or by Alex, Drew and Melody. The original songs fit seamlessly into the setlist they created for the day. Melody Trucks singing the national anthem was a great way to kick off the festival.
Saturday’s lineup featured Melody Trucks & The Fitzkee Brothers Band, Fireside Collective, Sister Sadie, Jammy Buffet, Shadowgrass, Yonder Mountain String Band and Little Feat.
Grateful Web had an opportunity to sit down with Scott Sharrard, guitarist for Little Feat, to discuss what he and the band are up to on this leg of The Last Farewell Tour. Little Feat is one of those bands whose songs you recognize as soon as you hear the first few notes. Their new album, Strike Up the Band, is fresh, but the sound is familiar. Scott Sharrard shared the observation that “we’re out there still doing it.” Little Feat’s newest members and original members are all going strong, making music and playing live.
At Baygrass, the Little Feat setlist included well-loved Little Feat classics along with new songs from the newest album. Sam Bush joined the band on fiddle for “Sailin’ Shoes,” “Willin’,” “Dixie Chicken” and “Feats Don’t Fail Me Now.” Little Feat is a jam band, but they are also so much more. It’s always a great time seeing this band play live.
Day two of the festival started under overcast skies, with a half-hour downpour that ended just in time for opening band Geraldine to start the music festivities promptly at 11:15 a.m.
Geraldine is a local Maryland-based bluegrass band and a hometown fan favorite, having played Baygrass every year since its inception. Their set was well received, and they were accompanied onstage by two dancers who added an audience-participation element to the performance.
Midnight North were up next for their Baygrass Festival debut. Midway through the set, they were joined by Artists-at-Large Allie Kral on fiddle and Patrick Rainey on saxophone, along with special guest Cris Jacobs on lead guitar. The band, accompanied by Allie, Patrick and Cris, played a great version of “New Speedway Boogie” by the Grateful Dead. The audience thoroughly appreciated the opportunity to dance and enjoy the familiar Garcia-Hunter composition.
The day’s music continued with sets by TopHouse, Scythian and Mountain Grass Unit, followed by festival-ending sets from Béla Fleck My Bluegrass Heart and the Sam Bush Band.
On Sunday afternoon, Grateful Web had the opportunity to sit down with Drew Fitzkee, bass player for the Fitzkee Brothers, to learn a little about the band and its history. The brothers, Drew on bass and Alex on drums, both discovered their passion for music at an early age and have been following that calling ever since. A grade-school teacher introduced Drew to the bass guitar. He was intrigued, and Alex soon joined the fun on drums. The brothers have studied the genre, taken lessons and attended camps with some of the most talented and well-known musicians in the business. Drew’s enthusiasm for playing the bass guitar is infectious, and Alex’s drumming and vocals are spot-on. The Fitzkee Brothers are clearly dedicated to their craft. The festival fans see that dedication and enthusiastically support the brothers as they continue to grow as professional musicians.
In between sets, we attended a workshop on the History of Bluegrass featuring Sam Bush, John Bolton from Geraldine and Drury Anderson from Mountain Grass Unit. The moderator asked insightful questions, and the dialogue, anecdotes and interactions were lively and informative. Sam Bush’s knowledge of bluegrass history helped make this a unique experience for all the participants.
Right before Béla Fleck took the stage, Ron Katz, one of the festival organizers, shared some heartfelt observations about the history of the Baygrass Festival and its commitment to environmental stewardship. Much of what the festival provides is environmentally friendly, compostable or recyclable. Oyster shells are returned to the bay to continue the cycle of sea life.
Ron Katz highlighted this theme that runs throughout the festival’s DNA: “Every Jam Heals the Bay.” He also touched on a phrase, “Tikkun Olam,” often translated as “repairing the world.” That idea aligns perfectly with the Baygrass Festival: Let’s leave this place better than we found it.
Béla Fleck My Bluegrass Heart played a set that was thoroughly enjoyable. The band interspersed traditional bluegrass with a phenomenal bluegrass rendition of George Gershwin’s “Rhapsody in Blue,” along with a mashup of polka and bluegrass that Michael Cleveland on fiddle dubbed “Polkagrass.” They were also joined by Sam Bush for a fiddle duet with Michael Cleveland, two of the most accomplished fiddle players on the planet.
The final set of the festival belonged to Sam Bush and his band. Sam clearly loves what he does. His smile and passion for the music are infectious. Sam was joined for several of the closing songs by Allie Kral, Patrick Rainey and Cris Jacobs, making the musical collaborations throughout the weekend that much more memorable.
The Baygrass Festival has something for everyone. It’s a family-friendly festival, with a KidZone, face painting, artist workshops, Chesapeake Bay educational events, specialty food trucks and drink tastings, yoga on the beach and a sober meet-up safe space. The staff and volunteers are helpful, friendly, knowledgeable and caring.
The 2026 Baygrass Festival was two full days of great music on the picture-perfect shores of the Chesapeake Bay. The 2027 festival dates are set for September 18 and 19. Make sure you add the Annapolis Baygrass Festival to next year’s calendar.
