Experience one of the best Juneteenth events in Orlando! GRAMMY-winning artist Fy\u00fctch will host a special Juneteenth-inspired concert at OCLS branches celebrating community, Black history and culture through a blend of hip-hop, soul, R&B and pop! Recommended for ages 6-12.<\/p>\n Other Great Juneteenth Events in OrlandoKissimmee Juneteenth Festival<\/a>Date: Saturday, June 13, 2026, 12 p.m.-4 p.m.Location: Kissimmee Lakefront Park, 201 Lakeview Drive, Kissimmee, 34741Cost: FREE admission<\/p>\n The Kissimmee Juneteenth Festival is a community celebration of African American culture, including live music, delicious food, craft vendors, and exciting giveaways. Enjoy live music, food, the KUA Kids Power Zone, and a variety of local vendors. This family-friendly event is open to everyone and offers a welcoming space to learn, connect, and celebrate together.<\/p>\n Central Florida Juneteenth Gala 2026: The Legacy Ball<\/a>Date: Saturday, June 13, 2026, 5 p.m.-9 p.m.Location: Macedonia Missionary Baptist Church, 812 E Rollins St, Orlando, FL 32803Cost: $44.79<\/p>\n Join Veterans Heritage Youth Preservation Foundation for the Central Florida Juneteenth Gala 2026: The Legacy Ball, an elegant evening honoring heritage, celebrating freedom, investing in youth, and recognizing the historic legacy of Eatonville, Florida.<\/p>\n A Cabaret of Legends<\/a>Dates: Saturday, June 13, 8 p.m., and Sunday, June 14, 2026, 3 p.m.Location: Orlando Shakes, 812 E Rollins St, Orlando, FL 32803Cost: $49<\/p>\n A Cabaret of Legends is a thrilling musical journey celebrating the iconic voices that have shaped the world of entertainment. Tymisha Harris, with her undeniable charisma and \u201cvocal fireworks\u201d (CBC Montreal), pays homage to the greatest performers of all time, from soulful jazz to electrifying pop. Audiences can expect a non-stop spectacle of music, dance, and pure entertainment.<\/p>\n 11th Annual Juneteenth Celebration in Hannibal Square<\/a>Date: Sunday, June 14, 2026, 10 a.m.-2 p.m.Location: Hannibal Square Heritage Center, 642 W New England Ave, Winter Park, FL 32789Cost: FREE<\/p>\n Join the 11th Annual Juneteenth celebration, Threads of Freedom: Memory, Resistance, and Legacy. As you visit the Hannibal Square Heritage Center, participate in a community arts workshop led by Form 2 Fashion to experience the ancient art of quilting, followed by a panel discussion to learn how this art form preserves sacred histories. All materials will be provided for you to contribute to a lasting quilt that will be on display in the Heritage Center following Juneteenth.<\/p>\n History Alive: Famous Floridians<\/a>Date: Friday, June 19, 2026, 10 a.m.-5 p.m.Location: Orange County Regional History Center, 65 E. Central Blvd. Orlando, Florida 32801Cost: FREE admission<\/p>\n Celebrate Juneteenth at the History Center with this family-friendly day! Meet the trailblazers who shaped our region in unforgettable ways \u2013 from the musicians who lit up Orlando\u2019s South Street Casino to activists and community builders whose legacies continue today. Engage with the evolving story of freedom, join a guided museum tour, and enjoy hands-on activities that highlight the Black Floridians who helped elevate Central Florida\u2019s culture and history. Guided museum tours are available at 10:30am, 12pm, 1:45pm, and 3:30pm.<\/p>\n 2nd Annual Juneteenth Freedom Day Paint Party<\/a>Date: Friday, June 19, 2026, 4 p.m.-8 p.m.Location: Napasorn Thai Restaurant, 56 East Pine Street #UNIT 100, Orlando, FL 32801Cost: FREE admission for the first hour and for open mic and spoken word, additional ticket options starting at $13.32<\/p>\n Join for an evening of painting, vibing, and live entertainment, including an open mic and spoken word, DJs, and the opportunity to paint your own masterpiece (pre-drawn or freestyle). Ages 18+.<\/p>\n Sip & Paint by One of One Artworks<\/a>Date: Friday, June 19, 2026, 7 p.m.-9 p.m.Location: Twelve Talons Beerworks, 2807 East South Street, Orlando, FL 32803Cost: $28.52<\/p>\n Celebrate freedom, creativity, and community! It will be an unforgettable evening filled with art, music, great vibes, and connection. Whether you\u2019re an experienced artist or just looking for a fun night out, this guided paint experience is perfect for all skill levels. All painting materials will be provided \u2014 just bring yourself, your friends, and your creativity!<\/p>\n Lenox Ave at Judson’s Live<\/a>Dates: Friday, June 19, shows at 7 p.m. & 9:30 p.m., and Saturday, June 20, 2026, shows at 6 p.m. & 9 p.m.Location: Judson’s Live, 445 South Magnolia Avenue, Orlando, FL 32801Cost: Tickets starting at $55.76<\/p>\n The \u201cbiggest, brightest spot in town\u201d is coming to Orlando’s premiere music room, Judson\u2019s Live, in concert! Set in the Harlem Renaissance and based on the poetry of Langston Hughes, Lenox Avenue is a critically acclaimed celebration of black creativity, resilience, and above all\u2026JOY. After being named \u201cBest Show\u201d of 2025 Orlando Fringe, audiences will have an opportunity to experience a new version that will be submitted Off-Broadway. This production is presented in partnership with Central Florida Vocal Arts, in celebration of Juneteenth on June 19 & 20.<\/p>\n 4th Annual Eatonville Juneteenth Celebration<\/a>Date: Saturday, June 20, 2026, 12 p.m.-7 p.m.Location: Hungerford Field, 100 East Kennedy Boulevard, Eatonville, FL 32751Cost: FREE admission, $25 for VIP with drink tickets, reserved seating, and tasting card<\/p>\n Join for live entertainment, local vendors, history hunts, and youth STEAM activities. Plus, don\u2019t miss the Freedom Cookoff, where local chefs will compete with culinary creations inspired by Southern Black traditions.<\/p>\n Love & Liberation: A Boldly Unapologetic Juneteenth Pride Celebration<\/a>Date: Saturday, June 20, 2026, 2 p.m.-6 p.m.Location: Central Florida Fairgrounds, 4603 W Colonial Dr, Orlando, FL 32808Cost: FREE admission,<\/p>\n Juneteenth is about freedom. Pride is about authenticity. Together, they ignite a powerful tribute to identity, resistance, and liberation. This is Central Florida\u2019s largest Juneteenth Pride celebration \u2014 a bold, vibrant fusion of culture, resilience, and unapologetic Black queer excellence. You don\u2019t want to miss it!<\/p>\n ArtnB Paint & Sip Picnic<\/a>Date: Saturday, June 20, 2026, 4 p.m.-8 p.m.Location: \u00c0 La Cart \u2013 City, 274 N Orange Ave, Orlando, FL 32801Cost: Starting at $33.85<\/p>\n Celebrating Juneteenth with a vibe like none other. This is the liveliest Paint & Sip in Florida. Where art meets R&B, a day filled with RnB, dance, art, and vibes that touch the soul. Enjoy art, cocktails, vibes, and an all-around good time! Ages 21+.<\/p>\n![\"\"](\"https:\/\/www.newsbeep.com\/us-fl\/wp-content\/uploads\/2026\/06\/Orlando-Date-Night-Guide-600x240-03-2021.jpg\")
<\/a>Juneteenth Events in OrlandoFeatured Event: Fy\u00fctch \u2013 Summer at Your Library<\/a>Dates: Monday, June 15, and Wednesday \u2013 Friday, June 17 \u2013 19, 2026Locations:South Trail Branch \u2013 Monday, June 15, 10:30 a.m.Hiawassee Branch \u2013 Wednesday, June 17, 10:30 a.m.North Orange Branch \u2013 Thursday, June 18, 10:30 a.m.Eatonville Branch \u2013 Friday, June 19, 10:30 a.m.Cost: FREE<\/p>\n