Annapolis Songwriters Festival Headliners Announced!

Annapolis Songwriters Festival

Oh Crab...stay tuned for the 2026 date. 🦀

With legendary bars and intimate venues tucked along the waterfront, Annapolis hits all the right notes for live music fans looking to experience the heart of the Chesapeake Bay.

44 Calvert St, Annapolis, MD

Calvert Street Map

ASF

Music lovers, adventure seekers, and foodies, Anne Arundel County is calling your name and is more than just a festival stop! This vibrant destination, known for its stunning waterfront views, historic charm, and lively cultural scene, is turning up the volume just in time for our infamous Fall events line-up.

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What is Annapolis Songwriters Festival?

The Annapolis Songwriters Festival is modeled after the hugely successful Key West Songwriters Festival, which, going into its 30th year, continues to be the largest festival of its kind in the world. Highlighting the specialized craft that is the essence of music, this festival aims to give music lovers a chance to get to know the names and faces behind the songs in an up-close and personal setting.

Historic strolls, outdoor thrills, or local brews, what’s on your list?

From Anne Arundel Count to downtown Annapolis and Arundel Mills, there is much to explore while visiting for Annapolis Songwriters Festival. We invite you to an authentic Chesapeake Bay experience. Filled with seafood, sailing on the bay, history tours, and boutique shopping - all within walking distance of the U.S. Naval Academy. Venture to the BWI Entertainment District of the county for action-packed gaming, sports, and unique experiences. Plus, outlet shopping at Maryland's top attraction, Arundel Mills Mall.

Hotels

Restaurants

Walkable Downtown Annapolis

Plan Your Trip

What to Expect?

Bring your positive attitude, willingness to explore new music, state issued ID, and all your best friends!

You can expect to hear a wide variety of songs that you know and love and some that you may not recognize but be prepared to leave with some new favorites!

Kids 10 and under are FREE for Dirty Heads at the Calvert Street Stage.

And the lineup is...

ASF Artists 2025