Annapolis, Maryland's waterfront jazz festival turns five this year, and it's spreading the celebration across two weekends in November — the 6th through the 15th. The Annapolis Jazz & Roots Festival is based in Eastport, the maritime neighbourhood just across the water from downtown Annapolis, and uses eight venues in five different parts of the city. Expect centuries-old churches, a historic Black social club, a museum and a recreation centre, all within strolling distance of Chesapeake Bay views.
The 2026 theme, "New World Music: Centuries of Sound," frames the lineup as a story of American music from colonial times to now. That means everything from period-instrument colonial concerts to cutting-edge jazz, plus honest engagement with Maryland's history of slavery and indenture and the Indigenous roots of the region.
Weekend one opens Friday, November 6 at 7pm at St. Luke's Episcopal Church, where trumpeter Muneer Nasser — son of jazz bassist Jamil Nasser — honours three giants born in 1926: John Coltrane, Miles Davis and Randy Weston. Saturday brings a morning lecture at the Eastport-Annapolis Neck Library from Maryland State Archives historian William Kelly on slavery and indenture in colonial times, followed by two sets (4pm and 6pm) from Afro-Peruvian band Perkutao at the Peerless Rens Club. Sunday is a day of contrasts: David and Ginger Hildebrand play colonial music on period instruments at 2pm in a tribute to the Marquis de Lafayette, then drummer Makaya McCraven — who fuses jazz improvisation with hip-hop production — takes over Maryland Hall at 7pm.
Weekend two starts Friday, November 13 with the U.S. Naval Academy Band's Superintendent's Combo paying tribute to Miles Davis at Eastport UM Church, with a public reception after. Saturday morning, NYC jazz vocalist Vanessa Racci explores Italian contributions to American jazz at the library, then vocalist Akua Allrich headlines the Banneker-Douglass-Tubman Museum at 2pm, marking her new album Bonya and honouring Miriam Makeba and Nina Simone. Visitors can also catch the exhibition "She Speaks: Black Women Artists and the Power of Historical Memory." The festival closes Sunday, November 15 at 2pm with Uhwachi-Reh, an Indigenous dance troupe led by Louis Campbell of the Lumbee, performing in ceremonial regalia with live drumming at the Pip Moyer Recreation Center.
Why it matters: most events are free or low-cost, and all but two venues offer free on-site parking — rare for a festival of this depth. But reservations are strongly recommended, and you can book through instantseats.com. (The McCraven show tickets go through Maryland Hall directly.) For travellers, it's a smart excuse to see Annapolis beyond its famous sailing scene: colonial architecture, a walkable historic centre, and a programme that treats music as a way into American history rather than just entertainment.
Full programme details are at annapolisjazzandrootsfestival.com.
