Upcoming Events/Pop Up Shops
July 31- Aug. 2, 2026 • Great Lakes Grand Prix powerboat races on Lake Michigan
Washington Park on Lake Michigan
Michigan City, IN
Aug. 21-23, 2026 • Annual Harvest Festival at Lakeridge Winery live music, vendors, grape stomping, wine, beer and food
19239 US 27
Clermont, FL
Sept. 12, 2026 • Rock the Rocks Beach Market the original beach market at The Original Crabby Bills, live music, vendors, food and drink specials
401 Gulf Blvd
Indian Rocks Beach, FL
Sept. 26, 2026 • Howey-in-the-Hills Artisan Market at Mission Resort + Club live music, vendors, food and drink specials, resort guests and local shoppers welcome
10400 County Road 48
Howey-in-the Hills, FL
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
Oct. 10, 2026 • Indian Rocks Beach Oktoberfest live music, food trucks, vendors, activities for kids
Kolb Park from noon to 7pm
Indian Rocks Beach, FL
Oct. 16-18, 2026 • Venice Sun Fiesta food trucks, vendors, live music
Downtown
Venice, FL
Oct. 31, 2026 • LagoonFest vendors, family friendly annual event
Flagler Drive, downtown West Palm Beach, waterfront
West Palm Beach, FL
Nov. 7-8, 2026 • Pirates, Parrots & Paradise Festival featuring a Jimmy Buffett Tribute band, drinks, food trucks, vendor village, live music
Coachman Park
Clearwater, FL
Nov. 13-16, 2026 • Siesta Key Crystal Classic Sand Sculptures, drinks, food trucks, vendors
Siesta Key Public Beach
Siesta Key, 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
Dec. 12-13, 2026 • Mistletoe Market on Marco Island with food trucks and a variety of vendors, island style holiday shopping
Veteran’s Park
Marco Island, FL
More events coming! Check back soon for our updated 2026 schedule.