Englewood Pioneer Days

Name: Englewood Pioneer Days
Start: 2025-09-01T09:00:00-04:00
Location: Dearborn Street

Schedule

Mon, 01 Sep, 2025 at 09:00 am

UTC-04:00

Location

Dearborn Street | Lehigh Acres, FL

Englewood Pioneer Days is an annual tradition taking place on Labor Day Weekend. See below for a list of events
Cardboard Boat Races
Saturday, August 30st at Indian Mound Park
Boat races start at 10:00am
Food & Drink will be available for purchase
Email [email protected] for Registration
*Cardboard Boat Race Organizers: Englewood Sailing Association, Lasbury Tracy Realty and St. David’s Jubilee Center
Parade
Monday, September 1st
Pioneer Day Parade **Englewood History Theme**
Parade Start time 9:00am
Staging at 240 S Indiana Avenue – Arrive as early as you need to in order to be ready by 9:00am.
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.
Email [email protected] for Registration
After Parade Festivities
After Parade Festivities at Pioneer Park
Starts post parade, approximately 10:00am
Pioneer Park – 325 W Dearborn Street
Schedule of Events
10:20am – Announce Parade Winners
Hosted by Englewood Chamber
10:30 – Diaper Derby @ 10:30am
Hosted by Lemon Bay Woman’s Club
11:00am – Live Music
Hosted by Dale Shumate
11:30am – Pie Eating Contest
Hosted by Amy Gonzalez, Jennie Joyce and The Dearborn Coffeehouse
12:00pm – Live Music
Hosted by Dale Shumate
12:30pm – Watermelon Eating Contest
Hosted by The Dearborn Coffeehouse
1:00pm – Live Music
Hosted by Dale Shumate
Children’s games & activities will be taking place in the Plaza from 10:00am to 1:00pm.
Vendors
Vendors will be set up from 10:00am until 1:00pm at Pioneer Plaza
– Children’s Games & Crafts: GFWC Rotonda Woman’s Club
– Englewood Chamber of Commerce
– More to come
– Email [email protected] for Vendor Application
Grand Marshals
2025 Grand Marshal (Individual)- TBD
2025 Grand Marshal (Organization) – TBD
Mayor Candidates:
TBD
Each Mayor Candidate may have other fundraising events they plan and schedule. Their duties will be to ride in the parade and be part of the Pioneer Day events. The Mayor wears the sash to events and promotes how special Englewood is! Jeannie Joyce is the chair the of the committee – “My takeaway is that all the charities win because they get to keep what they raise and they get to spotlight their charities to the public and raise awareness.” The committee consists of Mike Dalke, Cyndi Fredricks and of course Jeannie Joyce to help plan and promote the events. In the past the money raised has helped so much as well as charities that were previously unknown were brought to the forefront of the community. Please reach out to Jeannie Joyce with any questions or call 360-431-6910.