Upcoming Events/Pop Up Shops
May 15-17, 2026 • 4th Annual 2026 Invitational Bike Show
live music, food, drinks, vendors, hours vary: Friday 5-8, Saturday 10-8 and Sunday 10-4
OCC Road House & Museum, 10575 49th St. North
Clearwater, FL
May 16, 2026 • Siesta 7’s Epic Rugby Tournament at Siesta Key
live music, cold drinks, vendors, epic rugby all day on the sand
Siesta Key Public Beach
Siesta Key, FL
May 30, 2026 • The Sarasota Margarita Festival
live music, cold drinks, vendors, food trucks, the world’s largest margarita festival tour, one day only, hours noon to 6pm
hosted by Big Top Brewing Co. • 3045 Fruitville Rd.
Sarasota, FL
June 6, 2026 • Hukilau Legendary Tiki Festival live music, food, drinks, vendors
Beachcomber Resort
Pompano Beach, FL
June 27, 2026 • Sarasota Key Quest Festival (a fundraiser for 1CheckAway.org)
live music, food, drinks, vendors
Bayfront Community Center Civic Greens Lawn, 803 N. Tamiami Trail
Sarasota, FL
July 31- Aug. 2, 2026 • Great Lakes Grand Prix powerboat races on Lake Michigan
Michigan City, IN
Oct. 3-4, 2026 • Melbourne Fall Craft & Marketplace Expo live music, food trucks, vendors
Wickham Park
Melbourne, FL
Oct. 8-11, 2026 • Englewood Beach Waterfest (2026 APBA Championship Final) Southwest Florida’s Premier Celebration of Everything Water! Boat races, food trucks, vendors
Englewood Public Beach
Englewood, FL
Dec. 5-6, 2026 • Mistletoe Market on Anna Maria Island with food trucks and a variety of vendors, island style holiday shopping
City Field
Anna Maria Island, FL
More events coming! Check back soon for our updated 2026 schedule.