+ By Dylan Roche
Imagine being in downtown Annapolis during a beautiful late-summer weekend, and venues throughout the area are filled with the sounds of song—a mix of genres, of styles, of vocal ranges. You make your way from bar to theatre to historic building. Maybe you stop by an outdoor space or hop aboard a cruise. Everywhere you go, there’s a songwriter performing. Perhaps it’s someone who has written for several big-name stars that anyone around the world would recognize or it’s a talented local enjoying their last bit of obscurity before fame discovers them. For four days, you can explore the area, hearing music and even engaging with these talented songwriters, learning what inspires them or what guides their process.
This is the type of experience someone has at the Annapolis Songwriters Festival, which enters its fourth year in 2025 and runs from September 11 through 14. A project handled by the team at Rams Head Presents, the festival is modeled after the Key West Songwriters Festival in Florida, which has been a tradition for nearly 30 years. When Rams Head Presents bought the Key West Songwriters Festival a few years ago, there was a clear next step: create something similar and bring that kind of experience to the historic capital of Maryland, according to Kris Stevens, Rams Head Presents’ vice president of programming, who handles all the talent buying and booking for the company. “We are surrounded by songwriters,” she says. “We are lucky to have so much talent in this area.” Because she’s been booking artists for Rams Head Presents since 1998, she knows what kind of talent the Annapolis community has access to, either close to home or from farther away. And with four or five performance slots per day at fifteen different venues over the course of the festival, she has the opportunity each year to invite a varied, interesting lineup. “People love performing in Annapolis, and they love this festival,” she adds.
The beauty of Annapolis is part of the festival’s charm. Having the performances spread out across the city’s general downtown area and out to Maryland Hall allows festivalgoers to explore. “When you hear ‘music festival,’ you think you’re going into one spot and there are a few stages,” says Royal Bundy, Rams Head Group’s vice president of marketing. “When you see the lineup, it’s not like you go to one space and see everyone on the poster. You’re going to [many] different venues.” Worth noting is that most of the performances are free, and there’s a total of hundreds of hours of entertainment and engagement over those four days.
Some of the past big names who’ve played the venues at Annapolis Songwriters Festival include Jake Owen, the country singer known for “Yee Haw” and “Startin’ with Me,” and Rob Ragosta, who has written songs for the rapper Jelly Roll. Other past acts include Blondie, Citizen Cope, JJ Grey, James McMurtry, Fantastic Negrito, Johnnyswim, LeAnn Rimes, and Avery*Sunshine.
The music industry is a diverse environment that includes songwriters who perform the works that they write and songwriters who write songs that other people perform, such as with Ragosta. Some music fans may be surprised to discover that a songwriter wrote music for several different artists, and even though those songs are popular or even ubiquitous, the songwriter’s name might not be associated with the song as much as the singer is. The festival provides an opportunity for music lovers to listen to singer-songwriters perform the music that they wrote. There’s also the chance to engage with the writers in talkback sessions or writers’ rounds to hear about their inspiration and their process.
Bars and restaurants are not the only festival venues; there are also performances at Maryland Hall, the Banneker-Douglass-Tubman Museum, and the parking lot at City Dock, which boasted a full stage in years past, pre-construction (organizers are transferring that stage to Calvert Street, where Dirty Heads will be playing on September 12). Bundy recalls how sometimes she’ll mention to someone that there’s a performance at City Dock, and they’ll often reply with the same question: Which bar? “We have to explain we’re taking over the parking lot and turning this into a first-class venue,” she says. “It’s not going to feel like you’re sitting in a parking lot. We have state-of-the-art sound. We are turning this into an actual, real concert venue.”
Another unique venue is the Watermark water taxi. In past years, songwriter Sheena Brook—perhaps best known for her debut single “Bad Bitches Like Me”—has been on the water taxi around the harbor as it picks up and transports passengers, dropping them off wherever they want to go. For some of them, having a performing songwriter in the boat is a surprise, but they warm up quickly to the novelty of it. It’s not an everyday occurrence to be serenaded by a Grammy Award–winning songwriter while being taxied around the harbor. “It really is such a special experience and a way for people attending and at home to get to know a few of the writers on a deeper level, all while enjoying a beautiful view of Annapolis,” says Brook. “I ask them specifically about songs that have impacted them, and they perform them through my Bose S1 Pro+ live.”
Stevens explains how the festival provides a range of experiences, from the emotionally moving to the undeniably fun. “I’ve sat through several songwriter sessions and just been brought to tears by the poignant storytelling these people weave into their music,” she says. “There are the times when it’s intimate, or it can just be a party.”
One highlight of the weekend is the raffling off of a guitar signed by all the festival performers. The money raised goes to the nonprofit Annapolis Musicians Funds for Musicians, which provides temporary support to local musicians who cannot perform due to sickness, injury, or other circumstance.
This festival does what music and the arts are meant to do—bring communities together, tell stories, and celebrate talent. Having just completed the festival’s fourth year, the organizers are grateful for all of the collaborators who make it possible—not only the songwriters and attendees but also the venue owners, restaurateurs, hoteliers, and the many Annapolitans who are happy to see their city as a music destination. ν
For more information, visit annapolissongwritersfestival.com.
