The annual festival pays tribute to the founding families of the fishing village that straddles the Sarasota-Charlotte county line.

The 63rd annual Pioneer Days Festival and Parade features two weeks of free, family-friendly events, culminating in Florida’s longest-running parade.

The annual festival pays tribute to the founding families of the fishing village that straddles the Sarasota-Charlotte county line.

“Living the Dream” is this year’s theme, and festival president Chris Phelps and her army of volunteers have been busy putting the finishing touches on a plethora of events.

The highlight as always is the Labor Day parade, and a two-day street festival featuring music, food and fun in Dearborn Street’s Pioneer Park. 

THE SCHEDULE

Saturday: Little Miss/Mr. Englewood Pageant

The pageant moves to a new venue, the fellowship hall at Englewood United Methodist Church, 700 E. Dearborn St. E. Generations of Englewood residents have competed in this annual contest, which started in 1971.

Sunday: Community Charity Bowl

Dozens flock to Englewood Bowl, 299 S. Indiana Ave., to beat the heat, bowl and raise money for their favorite area charities. The event takes place from 2 to 6 p.m. Cost is $4 per game plus shoe rental.

Aug. 23: Kids Shipwreck Dance Party

The popular children’s Shipwreck dances move this year to the new rec center at Ann & Chuck Dever Regional Park, 6791 San Casa Drive. The free dance party for children ages 9 to 13 runs from 6 to 9 p.m. Attendees are encouraged to dress in the “Living the Dream” theme.

Aug. 24: Chalkfest 8.0

This popular hands-on event drew 650 attendees last year at its new location, the Orange Street Rec Center, 101 Orange St. Registration starts at 8:30 a.m. and all-day chalking starts at 9 a.m. on the playground. “This event has turned out to be a home run,” Phelps said.

Aug. 24: High School Shipwreck Dance Party

This free party caters to teens ages 14 to 18. The venue is the new rec center at Charlotte County’s Ann & Chuck Dever Regional Park, 6791 San Casa Drive.

Aug. 25: Kids Fish-A-Thon

Red tide forced the cancellation of this popular event last year. The free fish-a-thon for children 12 and younger kicks off early at the Tom Adams Bridge Fishing Pier. Signup starts at 7 a.m., with lines in the water at 8:25. The catch-and-release tournament is in its 10th year. 

Aug. 25: Historical Tour of Englewood

Take a self-guided tour of noteworthy homes and businesses of Englewood’s pioneer families. An online map available at englewoodpioneerdays.com will guide participants to stops along the tour.

Aug. 31: Cardboard Boat Races

Last year, this event was forced to move to the pool at Ann & Chuck Dever Regional Park because of red tide. Phelps said the venue proved so popular that Pioneer Days is permanently moving this perennial favorite event to the pool. Registration opens at 8:30 a.m., gates open at 9 a.m., and races start at 10 a.m. Seating is limited, so bring a chair.

Aug. 31: Adult Shipwreck Dance Party

The free “Shipwrecked in Englewood” dance party starts at 5:30 p.m. with the Englewood Drum Circle at a location to be named on Aug. 21. This event was revived in 2011 and pays tribute to the early festival’s street dance. Food and drink will be offered for sale with entertainment by Saint Tone, a high-energy rock dance band. “Living the Dream” costumes are encouraged.

Sept. 1-2: Pioneer Days Festival

Noon to 8 p.m. Sept. 1 and 8 a.m. to 3 p.m. Sept. 2 at Pioneer Park, 300 W. Dearborn St. The two-day event draws a crowd downtown with food, drink and music from some of the best local bands.

Sept. 1: Diaper Derby

Generations of Englewood residents have competed in the annual crawl at the Lemon Bay Woman’s Club, corner 51 N. Maple St. in Old Englewood. The diaper-clad babies will crawl at 2 p.m. No walkers allowed! Remember, that baby has to crawl.

Sept. 1-2: Car show

The open car show is from noon to 6 p.m. Sept. 1 in the 300 block of Dearborn Street. Southwest Florida’s Corvette Show starts immediately after the parade from 11 a.m. to 2 p.m. Sept. 2. Registration is free for entrants with prizes awarded in multiple categories for both shows.

Sept. 2: Pioneer Days Parade

The 63rd annual parade steps off at 9 a.m. on Labor Day and continues down Dearborn Street. “Living the Dream” is the theme of this year’s parade, which is the oldest continuously running parade in the state of Florida, and this year's parade grand marshal is Bobbi Sue Burton of Project Phoenix. Thousands attend the parade each year, so come early to get a good viewing spot.

 

For more information on each event, go to englewoodpioneerdays.com.