The Annapolis Songwriters Festiva takes over City Dock in September. Photo by Evan Dvorkin.
Jordan Sokel performs at last year’s festival. Photo by Glenn Miller.
Fifteen venues. One hundred and thirty performers. Eight ticketed shows. Four days of free, live music all over town. Best of all, the chance to hear talented composers play their songs as they originally wrote them. From September 11–14, the Annapolis Songwriters Festival rolls out its fourth annual tribute to extraordinary tunesmiths.
“The festival transforms the city into a music town for the weekend,” says Kyle Muehlhausen, owner of Rams Head Group, which is the parent company of Rams Head Presents. “What I take the most pride in is that we’re really celebrating the art of songwriting. Rams Head has played a big part in bringing national entertainment to Annapolis, and this elevates our local arts scene even further.”
Annapolis musician Jordan Sokel, who’s performed at past Songwriters Festivals, agrees. “It’s a great vibe. The city swells up with live music fans, and everyone seems to enjoy the camaraderie between the artists and the intimate nature of the showcases,” he says. “It’s great for the local economy and [gives] local artists the freedom to play their original material outside the normal bar-gig setting.”
With an open-air main stage on Calvert Street, acoustic sets in bars, restaurants and hotels, and ticketed performances at Rams Head, Maryland Hall, and beyond, the festival extends well beyond Rams Head’s West Street headquarters. Even the sidewalks take on a Nashville air, welcoming troubadours with guitars on their backs and cowboy hats on their heads.
The Annapolis event is modeled on the long-running Songwriters Festival in Key West, which celebrated its 29th year in May. Rams Head acquired the Key West festival four years ago and quickly adopted the setup for its home-town audiences.
“We get to know a lot of artists through the Key West event,” Muehlhausen explains. “We also have a partnership with BMI out of Nashville, who reps a lot of these songwriters. They help us in the selection process.
“One of my favorite things about the festival is that audiences get exposed to new artists every time, from Hall of Famers to a whole host of new and up-and-comers. We mix the local artists with more established ones, to help them in their journey to be successful.”
At every location, Muehlhauser says, the spotlight is on songwriters performing their own compositions, many of which have been recorded by other artists. “Most of the music is acoustic—just a singer and a guitar on the stage. Audiences get to hear the creation stories, how the song came about, what it means to the writer.”
It’s a winning formula, and one that attracts more than 25,000 visitors to the city over the course of the weekend. “We had to sell the bars and restaurants on the idea originally,” Muehlhausen recalls, “but now they see the benefits, and everyone wants to come back.” Headliners for 2025 will include 10,000 Maniacs at Rams Head On Stage and the Steep Canyon Rangers at Maryland Hall.
This year, the festival expands to Eastport, with two new venues at Blackwall Hitch and Boatyard Bar & Grill. The Banneker-Douglass-Tubman Museum joins the line-up, too. Offstage, two workshops at Maryland Hall will present sessions on the songwriter’s craft—one for children and one for adults. On the festival fringes, there’ll be live karaoke on water taxis and a special Bose listening lounge for audiophiles.
Joey Hyde and Sonia Leigh perform at City Dock during last year’s festival. Photo by Glenn Miller.
As in previous years, the 2025 fest will include a special fundraiser for AM-FM, the Annapolis Musicians Fund for Musicians. The nonprofit organization provides temporary financial relief to professional Annapolis musicians who cannot work due to sickness, injury, or other circumstances.
“AM-FM was a natural fit. We’ve presented some of their shows at Rams Head and always had a great relationship. They seemed like the perfect organization to support through our guitar raffle,” Muehlhausen says. The guitar is signed by each of the artists participating in the festival; patrons can take a chance on winning by purchasing raffle tickets online or in the Rams Head app.
Muehlhausen admits to having a few favorites in the festival lineup. “I’m looking forward to Dirty Heads, who will play on September 12 at the Calvert Street stage. Another act I’m very excited to see is Jeffrey Steele, one of the best storytellers. Twinnie is an up-and-coming artist, always a great performer. It’s a pretty diverse schedule.”
Annapolis music fans of every stripe, from rock to bluegrass and country, will find lots to like in this song showcase. See the complete festival schedule and buy tickets online at annapolissongwritersfestival.com.
