Annapolis Jazz & Roots Festival Returns with Diverse Music and Cultural Events

A Vibrant Return to Annapolis in November

The picturesque Chesapeake Bay and the historic city of Annapolis form a captivating setting for the anticipated Annapolis Jazz & Roots Festival, taking place over two weekends from November 7 to 16. In its fourth installment, this festival, rooted in the maritime neighborhood of Eastport, will broaden its scope by 2025 to include eight venues across the region. Most of the performances will be open to the public at no cost, while select events will require tickets, with reservations encouraged to secure a spot.

Festival Theme and Artistic Tribute

This year’s festival theme, “World Travelers & Hometown Heroes,” pays homage to the legacies of influential Maryland artists across music, dance, and visual arts. Figures like Eva Cassidy, whose musical prowess touched the world, and Eileen Carson Schatz, founder of the Footworks Percussive Dance Ensemble, are celebrated for their enduring impact despite no longer being with us. The lineup features a mix of international and local talents dedicated to sharing these stories through compelling performances.

Weekend One Highlights

• November 7, Opening Night: Held at Peerless Rens, a historic Black social club in Eastport, the opening features a Tribute to Eva Cassidy with performances by Alexis Tantau, Letitia VanSant, and Rusty Sal. Two showtimes are available at 6:00 and 8:00 p.m. Tickets range from $25 in advance to $35 at the door. Light refreshments will be available.
• November 8, Art and Music: The Banneker-Douglass-Tubman Museum hosts the “Sacred Spaces” exhibition by artist Jabari Jefferson, followed by a discussion on the interplay between music and visual art featuring Jefferson and his father, musician J.C. Jefferson. Later, J.C. Jefferson's Quartet pays tribute to the legendary Quincy Jones.
• November 9, Soulful Sounds: Michael McHenry Tribe, a funky rock trio known for collaborations with The Jacksons and George Clinton, performs from 3 to 5 p.m. at the Pip Moyer Recreation Center.

Weekend Two Features

• November 14, Jazz’s Golden Era: The Unified Jazz Ensemble revisits the classic jazz era of Duke Ellington, Count Basie, and Benny Goodman at Eastport U.M. Church. Jazz enthusiasts are encouraged to dress in styles from the 1920s to 1940s to immerse themselves in the atmosphere of that era.
• November 15, Morning to Afternoon Events: The Ed Hrybyk Trio will perform “Bass Traditions,” celebrating jazz bass legends like Charles Mingus at the Eastport-Annapolis Neck Library, followed by a performance at the Unitarian Universalist Church featuring the Footworks Percussive Dance Ensemble. This event honors the late Eileen Carson Schatz and highlights her international influence in Americana music and dance.
• November 16, Festival Finale: The day begins with The Freedom Choir at St. Luke’s Episcopal Church delivering a captivating world music experience. The festival closes with the Joshua Redman Quartet performing material from Redman’s latest album, “Words Fall Short,” at Maryland Hall for the Creative Arts. Ticket prices range from $25 to $85.

Historical Context and Cultural Significance

Annapolis, known for its rich maritime heritage and as the home of the United States Naval Academy, has long boasted a vibrant cultural scene. The city’s connection to waterfront traditions, boatyards, and sailing communities complements its passion for music and the arts. Since its inception, the Annapolis Jazz & Roots Festival has grown from a localized celebration in Eastport to a broader cultural event. It has successfully brought together diverse art forms and celebrated both emerging and established artists while fostering community engagement.

Music festivals like Annapolis Jazz & Roots serve not only as entertainment but also as a platform that strengthens cultural identity and tourism appeal. The festival’s mix of historic homage and contemporary artistry places Annapolis on the map as a dynamic destination for cultural travelers. As festivals often boost regional economies by attracting visitors across seasons, this event highlights how music and local heritage create lasting tourism value.

Jazz and Roots Music: A Brief Insight

Jazz music, with its roots tracing back through African-American communities and evolving through decades of improvisation and fusion, perfectly symbolizes the spirit of innovation and storytelling. The genre’s historical connection with maritime and port cities like Annapolis aligns well with sailing aficionados who appreciate rich cultural experiences alongside water-based leisure.

Rooted music traditions emphasize community, storytelling, and regional pride—elements that are amplified by events such as the Annapolis Jazz & Roots Festival. For sailing enthusiasts, the festival complements the allure of coastal excursions by enriching the cultural tapestry that surrounds the bay’s sparkling waters and historic marinas.

Funding and Organizational Support

The Annapolis Jazz & Roots Festival operates under the auspices of the Annapolis Community Foundation. It benefits from the backing of various cultural and public organizations, including the Maryland State Arts Council and the Anne Arundel County Public Library & Foundation. Local communications partners and arts organizations contribute to in-kind support, enhancing the festival’s outreach and community integration. The festival’s artistic direction under Paula (Paulina) Phillips continues to shape its creative vision and community engagement.

Event Schedule Summary

Looking Ahead: Jazz Festivals and Coastal Tourism

Music festivals continue to be powerful drivers of cultural tourism, drawing crowds that enrich local economies and foster vibrant social exchanges. For destinations like Annapolis, with its sailing and boating heritage, events that blend artistic vibrancy and coastal charm offer visitors a multi-dimensional experience. Sailing enthusiasts, yacht charterers, and boat renters visiting the Chesapeake Bay area gain a unique opportunity to explore lively music scenes alongside sunlit waters and marinas.

The success of the Annapolis Jazz & Roots Festival demonstrates how cultural activities and maritime lifestyle converge to elevate a destination’s appeal. As this festival expands in scope while preserving its hometown roots, it underscores the growing synergy between yachting communities and arts-based tourism, inviting visitors to enjoy both the pleasures of boating and the richness of live performances.

For those planning a visit to the Chesapeake Bay area during the festival season, the blend of exhilarating sailing activities and engaging festival programs presents an exciting itinerary. The waters of the bay, alongside marinas filled with superyachts and sailing boats, become the perfect backdrop for musical explorations and cultural celebrations.

Whether setting sail on a yacht or attending a homegrown music festival, the Annapolis Jazz & Roots Festival promises a remarkable chapter in the ongoing story of this coastal city’s vibrant life.

For international visitors and locals alike, GetBoat.com offers access to a wide selection of sailing boats and yachts for rent, complementing musical festivity with memorable cruising experiences that suit every taste and budget along the Chesapeake and beyond.