Music Festival Draws Songwriters to Annapolis

By Duffy Perkins

The first-ever Annapolis Songwriters Festival kicks off Thursday, Sept. 15, with almost 90 live shows scheduled over three days. Venues are lined up in what is being called a “Songwriter’s Trail,” a meandering sequence of event spaces, bars, and restaurants that begins at the Westgate Circle and eventually deposits at City Dock. Most of the shows are free, but larger shows held at Maryland Hall, Rams Head on Stage, City Dock, and Watermark Journey’s Songwriters on the Severn require paid tickets.

Indie folk singer-songwriter Amos Lee and country music superstar Jake Owen headline the festival, with shows at Annapolis City Dock on Friday and Saturday, respectively.

While big names such as Lucinda Williams, Josh Ritter, Robert Randolph, and James McMurtry may be familiar to many there are an additional 80 musicians on the schedule, local artists familiar to the Naptown music scene as well as some brand new faces.

To get a better idea of the festival and which shows should not be missed, we turned to Jimi Davies, the man behind Jimmie’s Chicken Shack and someone who is very much responsible for cultivating the Annapolis live music scene over the last three decades. While he takes his Hype Man responsibilities very seriously, Davies will share the stage each night of the festival with other local artists.

“We’re going to play a different type of show,” he says. “I’m hoping that everybody will do a song in a round, and we can delve into the inspirations of songwriting and bring everybody behind the scenes a bit. The songwriting process can take years, or it can take five minutes. Maybe the song I perform will have started out in a totally different style.”

Davies emphasizes that a songwriters festival is significantly different than a regular music festival because the musicians involved are not generally performing artists. It’s possible to hear a Grammy-winning hit in a completely different way.

“I’m hoping artists will go into storytelling mode,” he says. “I appreciate hearing other peoples’ processes as well.”

The Annapolis festival is modeled after the successful Key West Songwriters Festival, now in its 26th year. Both cities are a paradise for sailors and have excellent live music scenes. But there is a significant difference between the two festivals: the Key West festival generally does not promote local artists, whereas the Annapolis festival prioritizes local talent.

Davies consulted on bringing in local talent for the festival, and he was pleased when they took his list and added significantly to it. “My hope is that at least one artist will get their foot, or even just their big toe, in the door of some songwriters working out of Nashville or LA,” he says. “It’s just a whole different type of business. But I would love it if some of the non-local artists would recognize the talent of the people they’re playing with and give them some tips for making it in this very difficult industry.”

So who is Davies looking forward to hearing? He’s playing with Jen Van Meter, Dean Rosenthal, and Dave Tieff, local legends with their own cult followings. But he’s also excited to hear Daphne Eckman, Jordan Sokol, and Brandon Hardesty give a behind-the-scenes look at their creative processes.

As for judging the best venues around town, Davies is highly skilled in the art of the Vibe Check.

“Metropolitan is such a great venue for listening to new music,” he says. “They have a designated room which is intimate and so cool. Stan and Joe’s is the place for a fun band hangout with a saloon feel, and you can hear live music there every night of the week. Rams Head, both On Stage and the Tavern, is also phenomenal because it’s a listening venue, and is just set up for singer-songwriter stuff. It’s more intimate than you’d think.”

The Annapolis local music scene is easy to take for granted. “People who are from here don’t understand the wealth of talent we have,” Davies says. “People from outside Annapolis show up and say, ‘Wow. There’s something in the water here.’”

The festival will kick off on Thursday, Sept. 15 with Robert Randolph at the Maryland Cultural and Conference Center (MC3 Annapolis), located outside the Westin Annapolis on Westgate Circle. 

The event is presented by Rams Head, in conjunction with BMI, Visit Annapolis & Anne Arundel County, and the City of Annapolis. Schedule and tickets: