The 13th Annual UpTown Art Expo returns to beautiful Crane’s Roost Park on March 27th - 29th, 2026.
Discover amazing art, chalk street paintings, festival food and more! It’s a free admission art festival with free parking!
Plus, UpTown Art Expo presents live music all weekend long featuring Completely Unchained, Knighsnake, The Broken Hearts, Rockit Fly, The Smoking Jackets Trio and The Ultimate Santana Tribute.VIP seating available for purchase in front of the concert stage.
Enter below for your chance to win two VIP general admission tickets for Friday night (3/27) with Completely Unchained and Knightsnake. Plus, qualify for the grand prize upgrade to the front row.
To purchase tickets, click here.
NO PURCHASE NECESSARY. 3/4/26 - 3/22/26. Open to Florida residents of Orange, Seminole, Osceola, Lake, Polk, Brevard, Volusia or Brevard Counties, age: 18+. To enter, complete the Official Entry Form above. Up to five winners (four secondary and one grand prize) will be selected. Odds vary. Secondary Prize: Two VIP general admission tickets for tribute band concert at Uptown Art Expo on 3/27/26. Grand prize: two tickets VIP front row tickets for tribute band concert at Uptown Art Expo on 3/27/26 ARV = $60. For full rules, click here. Sponsor: Cox Radio, LLC including d/b/a WMMO-FM, 4192 N John Young Parkway, Orlando, Florida, 32804.