Know Before You Go: Annapolis Songwriters Festival

Annapolis is turning the volume up! The Annapolis Songwriters Festival, presented by Rams Head Presents in partnership with BMI, Visit Annapolis & Anne Arundel County, and the City of Annapolis, brings music to the bay. Taking place September 11-14, the festival transforms our historic waterfront capital into one giant jam session with four days of music, stories, and unforgettable performances.

Inspired by the world-famous Key West Songwriters Festival, this event celebrates the craft of songwriting and gives music lovers a chance to hear great songs, but the stories behind them. Picture strolling down cobblestone streets, hopping from cozy taverns to open-air stages, catching big-name headliners and discovering the next artist you’ll add to your playlist—all within walking distance of City Dock. 

Headliners You Won’t Want to Miss

This year’s concert series features a host of talented musicians and bands from across the country.

Highlights include:

• Steep Canyon Rangers (Sept. 11, Maryland Hall) – Kicking things off with Americana energy.
• Dirty Heads with Ballyhoo! & The Wheeland Brothers (Sept. 12, Calvert Street Stage) – A reggae-rock party in the heart of downtown.
• Al Jardine & The Pet Sounds Band (Sept. 13, Maryland Hall) – A Beach Boys legend brings surf vibes to the bay.
• 10,000 Maniacs (Sept. 13 & 14, Rams Head On Stage) – Two intimate nights with the alt-rock favorites.
• Songwriters on the Severn (Sept. 13, Watermark Cruise) – A floating concert featuring The Rum Strummers and The Garrett Boys.

Venues you’ll love: Maryland Hall, Rams Head On Stage, the new Calvert Street Stage, Banneker-Douglass-Tubman Museum, Watermark Cruises—and more throughout downtown.

Free Music Around Every Corner

One of the best parts? You don’t need a ticket to soak in the music. Free showcases pop up all weekend long at Annapolis favorites like Rams Head Tavern, Galway Bay, Red Red Wine Bar, Metropolitan Kitchen & Bar, Stan & Joe’s, Graduate Annapolis, and more.

This year there’s free sets across the bridge in Eastport at Boatyard Bar & Grill and Blackwall Hitch. Lace up your comfy shoes and follow the walkable “songwriters trail” from Maryland Hall to City Dock and into Eastport’s breezy bars and marinas.

Tickets, VIP, and Planning Your Festival

The Annapolis Songwriters Festival is built to fit any kind of music fan, whether you’re dipping in for one show or going all-out.

Single-event tickets start around $20 and go up to about $300, depending on the artist and venue. Want to see Steep Canyon Rangers at Maryland Hall? Grab a ticket. Prefer to cruise the Severn with live music? Book the boat show.

The Platinum Pass ($579.63) is your “festival all-access.” It bundles together tickets to Steep Canyon Rangers, Dirty Heads (with a VIP pit, open bar, and free parking), two open-bar “Songwriters in the Round” shows at Rams Head On Stage, Al Jardine & The Pet Sounds Band, your choice of a 10,000 Maniacs performance, the Sunday showcase at the Banneker-Douglass-Tubman Museum, plus a festival swag bag.

Tip: Download the official festival app. It has the full schedule, artist bios, maps, and push notifications for last-minute surprises. It’s your backstage pass to keeping up.

Tickets, full lineup, and app info can be found on the Annapolis Songwriters Festival website.

Insider Tips for Festival-Goers

• Parking: Headliners bring crowds. Plan ahead with nearby garages: Gott’s, Whitmore, Hillman, Park Place, or the State Garage (free on weekends). Note: Gott’s Calvert Street entrance will be closed during Friday’s Dirty Heads show.
• Get the App: Download the festival’s official app for schedules, artist bios, and last-minute updates.
• Shoes: You’ll be on your feet and getting your steps in as you go from place-to-place to listen to music. If you wear heels, we salute your commitment, but bring Band-Aids.
• Stay Hydrated: Those long walks across the songwriters trail can wear you out. Pack a reusable water bottle to keep yourself going. 
• Plan Meals: Downtown restaurants will be buzzing. Make reservations where you can, or follow your ears to a showcase at a local bar with bites and brews.
• Mix It Up: Don’t just hit the big stages! Duck into a smaller showcase for a chance to hear rising stars up close.

The Annapolis Songwriters Festival is more than a weekend of music, it’s a celebration of the artists and their stories. You’ll meet the people who wrote the songs you’ve belted out in your car. You’ll stumble onto acts you’ve never heard of and leave obsessed. And you’ll see a side of Annapolis that pairs history, charm, and incredible food with live music at every turn. The soundtrack for the rest of the year is waiting! 

ABOUT RAMS HEAD

Founded in 1989, Rams Head Group is a family-owned and operated restaurant and entertainment company. Rams Head Group operates four restaurant locations in Maryland and one in Florida. Rams Head Presents owns and operates Rams Head On Stage in Annapolis, recognized as the Top Club under 500 seats worldwide by Pollstar Magazine. Rams Head also provides programming for Maryland Hall for the Creative Arts and venues in Key West, Florida. Rams Head Presents acquired the Key West Songwriters Festival in 2021. More information: ramsheadgroup.com / ramsheadpresents.com.