The 2nd Street Festival returns this fall, Saturday-Sunday, October 3-4, marking its 38th year in Downtown Richmond. The FREE annual festival, produced by Venture Richmond Events, celebrates the rich culture of the historic Jackson Ward neighborhood.
Each year thousands visit Jackson Ward to reminisce about the days when 2nd Street was the heart and soul of Richmond’s African American community and was known as “the Harlem of the South.” Today, Jackson Ward continues to be a thriving community.
The 2nd Street Festival is an annual celebration over two days that features three stages of live music and entertainment along with a Kidz Zone, popular food vendors, a marketplace and Artists Row to shop, and the Richmond Metropolitan Antique Car Club.
This year’s festival features headliner DJ Jazzy Jeff on Saturday, October 3, Plunky & Oneness on Sunday, October 4, and many other talented artists showcased over the two-day event.
“This year we’re so excited to bring two-time Grammy winner DJ Jazzy Jeff to Jackson Ward for a fantastic Saturday night show,” said Sharon Bassard, Events and Booking Manager at Venture Richmond. “And to wrap up the festival on Sunday, we have the amazing, community-oriented, and iconic Plunky! Plan your family reunion and tell your friends now–this is one event you won’t want to miss!”
Saturday’s Headliner, DJ Jazzy Jeff
DJ Jazzy Jeff has been an esteemed DJ, music producer and actor from the 1980’s through today. In the early 1990’s on the television sitcom The Fresh Prince of Bel-Air, Jazzy Jeff played a character who was Will Smith’s best friend. And as a musical duo, DJ Jazzy Jeff & the Fresh Prince had several gold and platinum-selling albums and singles in the late 1980’s and early 1990’s, becoming the first hip-hop act to receive a Grammy Award in 1989 for “Parents Just Don’t Understand,” and a second for “Summertime.”
DJ Jazzy Jeff is credited, along with DJ Spinbad and DJ Cash Money, with popularizing the transformer scratch method. He also played a pivotal role in the rise of “neo-soul.” As recently as 2025, DJ Jazzy Jeff was announced as one of the remixers for this year’s FIFA World Cup theme, representing Philadelphia.
Sunday’s Closing Performance, Plunky & Oneness
For over 55 years, native Richmond saxophonist, songwriter and producer J. Plunky Branch has been at the vanguard of Afro-centric jazz, funk, R&B, house music, and go-go, weaving these interrelated musical forms into a forward-looking message of empowerment, positivity, and cultural awareness.
Along with his band, Plunky & Oneness, he has appeared along with some of the biggest names in Black music, including Patti Labelle, Ray Charles, Earth Wind & Fire, Frankie Beverly & Maze, LL Cool J, Chuck Brown, and more. His song “Every Way But Loose” was a top ten soul music chart hit in London in the 1980’s and his hit single, “Drop,” was released in 2007.
J. Plunky Branch has also served as an administrator, lecturer, and teacher. Plunky is a two-time recipient of National Endowment for the Arts Jazz Fellowships and in 2017 was appointed to the Governor’s Task Force for the Promotion of the Arts in Virginia.
More information on the 2nd Street Festival and additional artists performing will follow later this summer. For up-to-date information about the 2nd Street Festival, please visit:
https://venturerichmond.com/our-events/2nd-street-festival
Venture Richmond Events, LLC is a subsidiary of Venture Richmond, Inc.