Madison Bailey live in Annapolis

Experience Madison Bailey live on September 29th

Madison Bailey, known for her role as Kiara Carrera in the Netflix series *Outer Banks*, is scheduled to perform at The Admirals Cup Annapolis on September 29, 2026. Bailey has recently begun pursuing a music career, with a style generally described as pop-infused country, incorporating elements of folk and singer-songwriter traditions. Her released singles demonstrate a focus on personal storytelling and melodic arrangements.

The Admirals Cup Annapolis is a waterfront venue located in Annapolis, Maryland. Originally constructed in 1985 as a restaurant and bar catering to the sailing community—Annapolis being a prominent sailing hub—it evolved into a dedicated live music space following renovations in 2018. The venue is known for its intimate setting and views overlooking Spa Creek. It frequently hosts regional and national touring acts across various genres, with a capacity estimated around 400-500 people. The building itself features both indoor and outdoor performance areas, capitalizing on the Annapolis waterfront location. It’s become a recognized part of the city’s entertainment landscape since refocusing on live performances.