On July 23, Annapolis' Songwriters Festival rolled out what organizers are calling its biggest lineup yet, setting the stage for a fifth-anniversary run across downtown from Sept. 10-13. Young the Giant is set to headline the Calvert Street stage, with the four-day slate stacking more than 115 artists in theaters, bars and waterfront spaces. The mix includes ticketed headliners, intimate songwriters in the round sessions and dozens of free performances strung along a walkable Songwriters Trail.
Festival Built Around Songs And Stories
The event is modeled on the Key West Songwriters Festival and leans into stripped-down, story-forward sets that put writers at the center, according to Annapolis Songwriters Festival. AXS lists Young the Giant on the Calvert Street stage on Saturday, Sept. 12, with both VIP and reserved ticket options available for that headliner.
Lineup Highlights And Local Faces
Local reporting says the roster tops more than 115 artists and ranges from national acts such as Josiah and the Bonnevilles, Valerie June and Maggie Rose to Annapolis favorites Nate Finn, Daphne Eckman, Dan Haas, Jimi Haha, Jordan Sokel and Skribe, according to Eye On Annapolis. Naptown Scoop also flags Young the Giant as the festival headliner and notes that the full Sept. 10-13 schedule will be revealed alongside more undercard announcements.
Free Shows And Where To Find Them
Many performances will be free and staged in bars, restaurants and outdoor spots along a dedicated "Songwriters Trail," while larger ticketed concerts land at venues like Rams Head and Maryland Hall, according to Visit Annapolis. The festival's walkable footprint is part of the appeal, letting audiences bounce between waterfront stages and intimate rooms to catch both emerging local songwriters and national performers without needing much more than good shoes and a game plan.
Tickets, Venues And Practical Tips
Tickets for selected headliners are available through the festival's ticketing page and third-party sellers. AXS lists the Young the Giant show, and Rams Head On Stage's box office can answer venue-specific questions. Expect downtown parking to be tight; organizers and longtime attendees suggest walking between nearby venues, booking lodging early and checking the festival app for day-by-day schedules.
Why This Matters
In its fifth year the festival is being pitched as a moment that helps cement Annapolis' reputation as a compact music destination that spreads live song across the historic downtown, per Eye On Annapolis. Fans eyeing September should keep an eye on official festival channels for the finalized lineup and ticket links as schedules are locked in.
