Photo Courtesy ‘Annapolis Songwriters Festival’
Annapolis Songwriters Festival 2025 Day 2 09-12-25
‘Annapolis Songwriters Festival’ Returns September 10 to 13, 2026; Fourth Annual Event Features Scores of Artists and Bands at Venues Large and Small
Annapolis, MD - The 4th Annapolis Songwriters Festival will be held September 10 to 13, 2026 at nearly two dozen venues around Annapolis, including Maryland Hall, Ram’s Head, Banneker-Douglass-Tubman Museum, Market Space, and Watermark Cruises.
The four-day event will feature nationally-known and acclaimed singers and songwriters at ticketed events as well as free music showcases. The event is modeled after the renowned Key West Songwriters Festival, in its 30th year in 2026.
Over four days in and around Annapolis, ticketed performances include:
- Songwriters-In-The-Round featuring Tia Sillers, Rebecca Lynn Howard, Elisha Hoffman, Jeff Middleton, Anthony David, Alex Amen, Chuck Mead, Jeffrey Steele on Sept. 11 at Rams Head On Stage
- Songwriters On The Severn featuring Lost Saints, Twinnie, Gowa Gibbs on Sept. 11 aboard Watermark Cruises
- Songwriters-In-The-Round featuring Tommy Sims, Justin Wilson, Dylan Altman, Jet Harvey, Jeffrey Steele, David Tolliver, Ruby Amanfu, Sam Ashworth, Young Fables, Maggie Rose on Sept. 12 at Rams Head on Stage
- Songwriters-In-The-Round featuring Garrett Boys, Meg Murray, Angie Miller, Laura Brino on Sept. 12 at Annapolis Summer Garden Theater
- Young The Giant with Daisy Grenade on Sept. 12 on the Calvert Street Stage
- Maggie Rose with TWINNIE on Sept. 12 at Rams Head On Stage
- Songwriters-In-The-Round featuring Lost Saints, Arlis Albritton, David Ryan Harris, Sara Jean Kelley, Maggie Rose, Sonia Leigh, Jesse Ruben on Sept. 13 at Rams Head on Stage
- Josiah and the Bonnevilles on Sept. 13 at Rams Head on Stage
- Valerie June on Sept. 13 at Maryland Hall
“Whether you’re headed to a ticketed showcase concert, or strolling the streets of downtown to hear free performances from upcoming singer-songwriters, this is a festival that not only showcases performers and welcomes music lovers, but allows Annapolis to shine,” said Annapolis Mayor Jared Littmann.
The event is presented by Rams Head, in conjunction with BMI, Visit Annapolis & Anne Arundel County, AM/FM (Annapolis Musicians Fund for Musicians), Maryland Sports Commission, HD Radio, and the City of Annapolis. The four days of music will include concerts featuring national headliners and many free showcases and concerts on docks and in hotels, parks, and bars. Tickets are on sale now through the official website: www.annapolissongwritersfestival.com.
There will be parking restrictions and road closures in the area of Calvert Street between Bladen and West Streets from Saturday, Sept. 12 at 4 a.m until Sunday at 2 a.m. West Street between Calvert and Church Circle will be closed to parking and vehicle traffic from 4 p.m. until midnight on Saturday, Sept. 12 for Dinner Under the Stars. Singer Songwriter Festival performances are scheduled during that road closure, weather permitting.
Free musician showcases are scheduled to take place in a walkable area, with unique stops along the way to feature all the extraordinary hidden gems of restaurants and shops in Annapolis.
The hugely successful Key West Songwriters Festival, which the Annapolis festival is modeled after, continues to be the largest festival of its kind in the world. Highlighting the specialized craft that is the essence of music, the Annapolis festival aims to give music lovers a chance to get to know the names and faces behind the songs in an up-close and personal setting while showcasing Annapolis as a destination for music lovers.
Facebook & Instagram: @annapolissongwritersfestival
ABOUT RAMS HEAD: Rams Head Group is a family owned & operated restaurant and entertainment company since 1989. Rams Head Group currently owns and operates four restaurant locations in Maryland: Rams Head Tavern in Annapolis, MD; Rams Head Roadhouse in Crownsville, MD; Rams Head Shore House in Stevensville, MD; Rams Head Dockside in Glen Burnie, MD and a fifth location in Florida: Rams Head Southernmost in Key West, FL.
Additionally, Rams Head Presents owns and operates Rams Head On Stage in Annapolis, Maryland which has been recognized as the Top Club under 500 seats in the world by Pollstar Magazine. Rams Head also provides programming for Maryland Hall for the Creative Arts in Annapolis, Maryland and Key West Theater and The Key West Amphitheater in Key West, Florida.
Rams Head Presents purchased the Key West Songwriters Festival in 2021. For additional information visit ramsheadgroup.com / ramsheadpresents.com
ABOUT BMI: BMI was founded in 1939 by forward-thinkers who wanted to represent songwriters in emerging genres, like jazz, blues and country, and protect the public performances of their music. Operating on a non-profit-making basis, BMI is now the largest music rights organization in the U.S. and is still nurturing new talent and new music. Additional information at BMI.com.
