The Annapolis Baygrass Music Festival has just announced the exciting addition of Cris Jacobs as a special guest musician for Sunday’s lineup. He will join a roster that includes already-announced acts such as Little Feat and Yonder Mountain String Band, among others.
“Baygrass is one of those festivals that just gets it right,” remarked Jacobs. “It’s a beautiful place, with fantastic people, and the musicianship is always outstanding. I’m really looking forward to being part of it again.”
This year marks the festival’s fourth installment, and it will be returning to its picturesque location at Sandy Point State Park, right along the Chesapeake Bay in Annapolis. The event is scheduled for Saturday and Sunday, September 19-20, 2026. Over the course of the weekend, additional notable bands are set to perform, including Béla Fleck: My Bluegrass Heart, Sam Bush, Mountain Grass Unit, TopHouse, Shadowgrass, SCYTHIAN, Sister Sadie, Fireside Collective, Midnight North, Jammy Buffet, Melody Trucks & The Fitzkee Brothers Band, Geraldine, and three Artists-at-Large: Allie Kral, Alvin Lee, and Patrick Rainey.
In a recent development, Jacobs has also become a co-owner of the 8 x 10 music venue in Baltimore, which recently changed ownership. This venue has been the performing ground for legendary acts such as Billy Joel, Nirvana, and Lenny Kravitz. Under the new ownership team—comprised of Jacobs, Rising Sun Presents (led by Chris Perella), and Dave Rather—the venue is set to undergo renovations. Despite this new venture, Jacobs is committed to performing at the Annapolis festival in September.
The Baygrass Music Festival will feature interactive workshops and exhibits throughout the weekend, focusing on music, ecological conservation of the Bay, and mental wellness. These activities will be held at the Workshop Pavilion and Bay Guardian Village.
As both a performer and participant, Jacobs will engage in one of the workshops titled “Mental Health Matters: A Conversation with Cris Jacobs & Guest.” This session will be guided by John Way, the founder of The VA WAY, focusing on overcoming obstacles, discovering purpose, and the healing journey through music. Jacobs, having navigated his own struggles with depression, aims to use his experiences to confront the stigma associated with mental health discussions.
Other workshops and exhibits at the festival include:
- From Bay to Ballad: The Story, Songwriting, and Live Performance of “The Secrets That She Keeps”
Hosted by Watershed Stewards Academy
Presented and performed by Benny “Burle” Galloway, Dave Johnston (of Yonder Mountain String Band), Allie Kral (Artists-at-Large), Cory Chubb (of Geraldine), and other musicians. - From Tradition to Tomorrow: Bluegrass at 80
This Talk & Tunes session will be hosted by acclaimed author Tim Newby and Rolling Stone writer Garret K. Woodward, featuring special musical guests to be announced. - Learn to Shuck Like a Pro at Baygrass!
Hosted by Oyster Recovery Partnership (ORP)
This popular workshop returns with delicious toppings provided by partner Ashling Kitchen. Participants will learn effective and safe oyster shucking techniques from experts.
For more information regarding these workshops, please visit the Annapolis Baygrass Music Festival website. Further details about workshops will be announced soon on the festival’s social media channels.
Annapolis Baygrass 2026 Daily Lineups:
SATURDAY:
Little Feat – Yonder Mountain String Band
Shadowgrass – Sister Sadie
Fireside Collective – Jammy Buffet
Melody Trucks & The Fitzkee Brothers Band
SUNDAY:
Sam Bush – Béla Fleck: My Bluegrass Heart
Mountain Grass Unit – TopHouse
SCYTHIAN – Midnight North
Geraldine
Both Days: Artists-at-Large
Allie Kral, Alvin “Uncle Al” Lee of The Lee Boys, and Patrick Rainey
Sunday Special Guest:
Cris Jacobs
Festival attendees can choose from several local lodging partners that offer premier hotels and campgrounds close to the venue. These accommodations are available at discounted rates on a first-come, first-served basis. Shuttle services will also be provided, connecting many lodging spots with the Annapolis Park-n-Ride.
Tickets for both two-day and single-day general admission, VIP passes, as well as pre-party tickets, are currently on sale at baygrassfestival.com.
