April Brown and After 5 Credit: Courtesy

Winter Park is set to celebrate Juneteenth right with Jazz & Jubilee this weekend. Attendees will dance to local musicians, eat delicious food and support local Black-owned businesses during this soiree.

Jazz musicians like the Franchise Players, Taurus Mateen and April Brown & After 5 perform throughout the night. Eats and drinks will be on offer from locals like chef Nicholas Allman and mixologist Catwinkle Holley, as well as vendors selling unique clothing, custom jewelry, art and more.

Early reserved seating has sold out for the event, but you still have time to RSVP for general admission entry.

5 p.m. Saturday, June 20, Shady Park, 721 W. New England Ave., Winter Park, equitycouncilcorp.org, free.

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This article appears in June 17-23, 2026.