Englewood Pioneer Days and Parade
- When: Saturday, September 5, 2026, 9:00 am
- Location: Multiple locations - see description - Englewood, FL
- Cost: Free
To celebrate the 70th year of Englewood’s beloved Pioneer Day Parade, the Theme will be 70’s Disco.
Englewood Pioneer Days is an annual tradition taking place on Labor Day Weekend.
Below, you will find information regarding:
– Cardboard Boat Races
– Diaper Derby
– Parade on Dearborn Street
– Family Activities at Pioneer Plaza
Cardboard Boat Races
9:00am Saturday, September 5th
Hosted by The Englewood Sailing Association and Lasbury Tracy Realty. Built boats will be ready for pickup at Lasbury Tracy’s office, 312 S. Indiana Avenue, on Monday the 24th and Tuesday the 25th. First come first served
Location Indian Mound Park 210 Winson Avenue
Food & Drink will be available for purchase along with music, festivities, pirates, prizes and fun!
Bring a folding chair and your community spirit.
Overflow Parking: Orange Ave and Green St – 4 blocks away. Stumpy’s Free Ride Shuttle will be offering rides beginning at 8:30am from the Green Street Parking Lot
Diaper Derby
Sunday, September 6th at 1:00pm-inside
Hosted by the Lemon Bay Woman’s Club – 51 N. Maple Street
Parade
9:00am Monday, September 7th
Pioneer Day Parade
Staging at 240 S Indiana Avenue – Arrive as early as you need to in order to be ready by 9:00am. Live Broadcast courtesy of WENG Radio-Fiorini Broadcasting
The Parade will run from Obee’s Parking lot down W Cowels Street, to McCall Road to Dearborn Street and finish at Veterans Memorial Pavilion.
After Parade Family Activities
After Parade Festivities at Pioneer Park
Starts post parade, approximately 10:00am
Pioneer Park – 325 W Dearborn Street
Schedule of Events
10:10am – Announce Parade Winners
Hosted by Englewood Chamber
10:30am – Pie Eating Contest
Hosted by Amy Gonzales, Realtor-Michael Saunders & Com. and The Dearborn Coffeehouse
10:45am – Watermelon Eating Contest
Hosted by Amy Gonzales and The Dearborn Coffeehouse
11:00am – Live Music
Hosted by Dale Shumate
Children’s games & activities will be taking place in the Plaza from 10:00am to 1:00pm.
- Website: www.englewoodchamber.com
- Category: Family Fun
All repeats 
