Englewood Pioneer Days

Englewood Pioneer Days is an annual tradition taking place on Labor Day Weekend.
Below, you will find information regarding:
– Little Miss/Mr. Englewood Pageant
– Cardboard Boat Races
– Parade on Dearborn Street
– Family Activities at Pioneer Plaza
– Beard Contest

Little Miss/Mr. Englewood Pageant
9:00am – 12:00pm Saturday, August 23th (Doors Open/Registration Starts at 8:00am)
Location – Sky Academy 871 S. River Road
Ages 0-12 years old
Click Here for More Information
Click Here for Application
Click Here for Questioner

Cardboard Boat Races
10:00am Saturday, August 30st
Location – The Sailing Center at 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 Cardboard Boat Registration Form & Waiver

Cardboard Boat Giveaway
10:00am Saturday, August 23rd at The Sailing Center located at Indian Mound Park
*Take home a free cardboard boat to paint and decorate. Deposit: pay $25 to take a boat home. Your $25 will be returned on race day Aug 30 when you come for the race.

This is your chance to get a cardboard boat for FREE that you can enter in the race. Built by the preeminent family of cardboard boat builders: Austin and Bart Tracy of Tracy Lasbury Realty. Bart and Austin have been building cardboard boats for Pioneer Day for decades!
*Cardboard Boat Race Organizers: Englewood Sailing Association, Lasbury Tracy Realty and St. David’s Jubilee Center

Diaper Derby
1:00pm Sunday, August 31st
Location – Lemon Bay Woman’s Club 51 N. Maple Street Click Here for Application

Parade
9:00am Monday, September 1st
Pioneer Day Parade **Englewood History Theme**
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.
Click Here for Parade Registration Form

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
10:30am – Live Music
Hosted by Dale Shumate
11:00am – Pie Eating Contest
Hosted by Amy Gonzalez, Jennie Joyce and The Dearborn Coffeehouse
11:30pm – Live Music
Hosted by Dale Shumate
12:00pm – Watermelon Eating Contest
Hosted by The Dearborn Coffeehouse
12:30pm – Beard Contest
Hosted by Sydney Martin
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 Family YMCA
– Prop It Up Photo Booths
– Englewood History Museum
– Englewood Amateur Radio Society
– 2 Minute Video Guy
– Coastal Fairy Hair
– Artist Colony

Dog Treats, Etc.
– Low Rider Dachshund Foundation

Snacks & Water
– Grace Community Church

Community Information
– Englewood Chamber of Commerce
– Sarasota County Mosquito Control

More to come
Click Here for Vendor Application

Beard Contest
Think you’ve got the longest beard in town? Prove it at our Longest Beard Contest! Whether it’s rugged, regal, or just downright impressive, bring your beard and compete for bragging rights and fun prizes. All ages welcome, let the whiskers win!
Click Here for Beard Contest Application

Grand Marshal
2025 Grand Marshal – Nancy Wille

Mayor Candidates:
Addison Morey – Junior Leadership Englewood
Darla Mapes – Englewood Recovery Oasis
Ed Kinsey – VFW Post 10178, Veterans Relief Fund
Lucy White – Englewood YMCA
Pet Samuels – Englewood Food Pantry
Sonnie Hall – Englewood Area Cancer Foundation

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 603-569-6419.