Another Pioneer Days is in the books, and this year was something special.
The 70th annual Englewood Pioneer Days filled Englewood, Florida with disco fever over Labor Day weekend, running September 5th through 7th, 2026. To mark the milestone, the whole town leaned into a playful “70s Disco” theme, with bright colors, big hair, and a lot of polyester.
Families and neighbors turned out in full force, packing three days with crafts, food stalls, live music, pirates roaming the streets, and parade entries dripping in disco flair.
Saturday kicked off with the ever-popular Cardboard Boat Races at Indian Mound Park, thanks to the Englewood Sailing Association and Lasbury Tracy Realty. Teams showed off their creativity (and, sometimes, a questionable sense of physics), cheering each other on as homemade boats bobbed and raced for the finish.
Sunday brought one of the festival’s cutest moments: the Diaper Derby, put on by the Lemon Bay Women’s Club. Carson K. took home first place, with Bodie A. following up in second, a photo finish.
Everything built up to Monday’s Pioneer Day Parade. Floats lined up at the Englewood Shopping Center, then rolled down Dearborn Street to the Veterans Memorial Pavilion, with WENG Radio broadcasting live as the crowd clapped and danced along.
And Pioneer Park and Pioneer Plaza buzzed with activity the whole weekend. The Englewood Chamber kept families busy with games and contests: pie and watermelon eating (hosted by Amy Gonzales and The Dearborn Coffeehouse) drew big, hungry crowds. Dale Shumate kept everyone movin’ with live music, rain showers or not.
A huge thank you to the Englewood Chamber and all the generous sponsors who worked so hard to pull off this amazing event for the Englewood community. Here’s to a fantastic anniversary bash. Can’t wait to do it all again next year.
