Celebrate 70 Years with a 70s Disco Theme!
This year is an extra-special celebration as the beloved Englewood Pioneer Day Parade celebrates its 70th year. And what better way to celebrate 70 years than by going full 70s?
The 2026 Pioneer Day Parade theme is 70s Disco, so expect plenty of groovy costumes, colorful floats, music, and retro fun as Englewood celebrates one of its longest-running community traditions.
Whether you’re spending Labor Day Weekend on Manasota Key, vacationing in Englewood, or you’re a local looking forward to the festivities, Pioneer Days offers a full weekend of family-friendly events.
Here’s what’s happening for Englewood Pioneer Days 2026.
SATURDAY, SEPTEMBER 5: CARDBOARD BOAT RACES
The weekend kicks off with one of Pioneer Days’ most entertaining traditions—the Cardboard Boat Races!
When: Saturday, September 5 at 9:00 AM
Where: Indian Mound Park, 210 Winson Avenue, Englewood
Hosted by the Englewood Sailing Association and Lasbury Tracy Realty, teams will put their homemade cardboard creations to the ultimate test and see which boats can stay afloat.
Even if you’re not racing, this is a fun event to watch. Food and drinks will be available for purchase, along with music, festivities, pirates, prizes, and plenty of community fun.
Bring a folding chair, find a spot near the action, and cheer on the racers.
Parking Tip: Overflow parking will be available near Orange Avenue and Green Street, approximately four blocks away. Stumpy’s Free Ride Shuttle will begin offering rides from the Green Street parking lot at 8:30 AM.
Register for the Cardboard Boat Races:
Download Registration form
SUNDAY, SEPTEMBER 6: DIAPER DERBY
Sunday brings an event for some of Englewood’s tiniest competitors!
The Pioneer Days Diaper Derby takes place indoors at the Lemon Bay Woman’s Club.
When: Sunday, September 6 at 1:00 PM
Where: Lemon Bay Woman’s Club, 51 N. Maple Street, Englewood
It’s a fun Pioneer Days tradition for families and definitely one of the weekend’s cutest competitions.
Register for the 2026 Diaper Derby:
Download application form
MONDAY, SEPTEMBER 7: 70TH ANNUAL PIONEER DAY PARADE
Get those bell-bottoms ready!
The highlight of the weekend arrives Monday morning with the 70th Annual Englewood Pioneer Day Parade.
When: Monday, September 7 at 9:00 AM
Theme: 70s Disco
The parade will begin near Obee’s parking lot, travel along W. Cowles Street to McCall Road, continue onto Dearborn Street, and finish near Veterans Memorial Pavilion.
The parade will also be broadcast live courtesy of WENG Radio – Fiorini Broadcasting.
With this year’s 70s Disco theme celebrating the parade’s 70th anniversary, spectators can expect Dearborn Street to be filled with creative floats, costumes, music, local businesses, organizations, and plenty of Englewood community spirit.
Register for the Pioneer Day Parade:
Download application form
THE FUN CONTINUES AT PIONEER PLAZA
Don’t head home when the parade ends!
The celebration continues immediately afterward at Pioneer Park and Pioneer Plaza, located at 325 W. Dearborn Street.
Festivities are expected to begin around 10:00 AM and continue until approximately 1:00 PM.
Pioneer Plaza Schedule
10:10 AM – Parade Winners Announced
Hosted by the Englewood Chamber
10:30 AM – Pie Eating Contest
Hosted by Amy Gonzales, Realtor with Michael Saunders & Company, and The Dearborn Coffeehouse
10:45 AM – Watermelon Eating Contest
Hosted by Amy Gonzales and The Dearborn Coffeehouse
11:00 AM – Live Music
Hosted by Dale Shumate
Children’s games, crafts, and activities will also be taking place throughout the Plaza from 10:00 AM to 1:00 PM.
FOOD, TREATS & LOCAL VENDORS
Come hungry! Pioneer Plaza will feature local food and drink vendors alongside community organizations and children’s activities.
Food and refreshment vendors currently include:
• 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 groups and activity vendors include:
• Englewood Community Coalition
• Englewood History Museum
• GFWC Rotonda Woman’s Club
• Lemon Bay Woman’s Club
• New South Window Solutions
• Neighborhood Land Conservancy
• Low Rider Dachshund Rescue
• Englewood Chamber of Commerce
• Englewood Amateur Radio Society
Additional vendors and activities may be announced as the event gets closer.
Vendor Application:
Download application form
