Annapolis Jazz & Roots Festival


Annapolis Jazz & Roots Festival

November 3-12, 2023


Escape to Annapolis this fall for the Annapolis Jazz & Roots Festival. Stay in historic downtown Annapolis or book a local short-term rental for two weekends of culture, history, and, best of all - jazz and live music


Michael Joseph Harris plays a guitar on stage (man in a black and white photo with a beard and wearing a hat)
Last year, Michael Joseph Harris of Hot Club Baltimore was a featured festival performer.
 Image courtesy of Annapolis Jazz & Roots Festival.



The greater Annapolis area was once known as a Jazz and Rhythm and blues stronghold with concerts at resorts such as Carr's and Sparrow's beaches from 1926 to 1974. Thanks to visionary developer Paul Pearson, who died in 2001, the King of France Tavern in the Historic Maryland Inn was a nationally prominent venue. Just a few blocks away, St. John's College was the home of the Annapolis Jazz Festival and iconic guitarist Charlie Byrd served as artistic director until 1996.

The Annapolis Jazz & Roots Festival will take place in Eastport, "the Left Bank of Annapolis," for this year's concerts. Building on this iconic history, a team of local leaders, including Mayor Gavin Buckley and Executive Director of the festival, Paulina Phillips, have revived this popular live music tradition to the delight of music lovers across the region. With an impressive slate of world-class international and regional artists, the festival will extend incrementally into downtown Annapolis in subsequent years.

The Venues

The Annapolis Jazz & Roots Festival will be spread over the first two weekends of November in Historic Eastport for the festival's inaugural year. Enjoy New Orleans Jazz at the Peerless Rens or a lecture at the Eastport-Annapolis Neck Library. St. Luke's Episcopal Church and Eastport United Methodist Church will also act as concert venues for the festival.


While you may come for the music, you should also make time to stay for the lectures. In addition to musicians Hazel Mitchell-Bell featuring Terry Koger and Halley's Hot Gumbo Swing Quartet, you will also be dazzled by the lecture from Chris Haley and the free performance by West African Drumming at the Eastport-Annapolis Neck Library. Reservations are required for all performances and lectures, but many offerings are free and family-friendly. Scroll for a list of events and to register.


a woman holding a saxophone
Halley's Hot Gumbo Swing Quartet


November 3, 2023 
Peerless Rens Club – Opening Concert         
Halley's Hot Gumbo Swingtet
New Orleans Jazz
TWO SHOWS: 6:00 PM & 8:00 PM
Reservations Required
Admission: $25


A black woman in African dress drumming
Nyame Nti, West African Drumming

November 4, 2023
Eastport – Annapolis Neck Library            
Nyame Nti
West African Drumming
Show: 11 AM
Reservations Required, register HERE!

A man holding a lyre over his shoulder
Ronn McFarlane & Ayreheart


November 5, 2023
Eastport United Methodist Church
Ronn McFarlane & Ayreheart
Music of the British Isles
Show: 4 PM   
Reservations Required, register HERE!




a man drumming

Enayet Hossain


November 10, 7 PM
St. Luke Episcopal Church
Melodic Intersect featuring Enayet Hossain, Greg Hatza & Hidayat Khan
Indian Fusion
Reservations Required, register HERE!


A black man smiling
Chris Haley is a renowned Author, Actor, and Academic.


November 11, 11 AM
Eastport - Annapolis Neck Library
Chris Haley
Lecture: ​“Indenture & Slavery in Maryland 1630's - 1864”


A black woman in a white dress smiling at the camera
Hazel Mitchell-Bell

November 11, 4 PM
Eastport United Methodist Church
Hazel Mitchell-Bell featuring Terry Koger
American Jazz
$20 advance, $25 at the door
*Veterans admitted free​
a man and a woman with gray hair singing


November 12, 4 PM
St. Luke’s Episcopal Church
Amoroso, Bossa Nova & Beyond with special guests Leonardo & Bruno Lucini