Englewood Pioneer Days

THE THEME FOR THE PARADE HAS BEEN PICKED!
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
Click Here for Registration Form

Diaper Derby
Sunday, September 6th at 1:00pm-inside
Hosted by the Lemon Bay Woman’s Club – 51 N. Maple Street
Click Here for Registration Form

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.
Click Here for Parade Registration Form

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.

Vendors
Vendors will be set up from 10:00am until 1:00pm at Pioneer Plaza
Children’s Games & Crafts:
– Englewood Community Coalition
– Englewood History Museum
– GFWC Rotonda Woman’s Club
– Lemon Bay Woman’s Club-Lemonade at the parade-Judges Booth-200 W. Dearborn Street
– New South Window Solutions
– Neighborhood Land Conservancy

— Low Rider Dachshund Rescue

Snacks, Water & Food
– Florida Bible Church
– Hippie Squeeze Lemonade
– Uncle Louie G’s Italian Ice & Ice Cream
– El Jo Bean Coffee
– Outside the Lunchbox
– The Portly Pirate
– The Sorbet Society

Community Information
– Englewood Chamber of Commerce
– Englewood Amateur Radio Society

More to come
Click Here for Vendor Application

Grand Marshal
2026 Grand Marshal – 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! Mike Dalke is the chair the of the committee The committee consists of Mary Jones and Amy Gonzales to help plan and promote the events. In the past the money raised has helped many charities that were previously unknown. The event brought them to the forefront of the community. Please reach out to Amy with any questions-360-431-6910.

Candidates will be announced July 27th with fundraising beginning August 1st.