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PLEASE NOTE: Due to Hurricane Dorian, the Pioneer Days Festivities, including Monday's Parade have been postponed. Please go to EnglewoodPioneerDays.com for updated information.
home : englewood pioneer days : please note: due to hurricane dorian, the pioneer days festivities, including monday's parade have been postponed. please go to englewoodpioneerdays.com for updated information.
October 23, 2019

8/30/2019 2:38:00 PM
Pioneer Days, 2019
Chris Phelps, Pioneer Days Organizer
Chris Phelps, Pioneer Days Organizer

When Chris Phelps says there’s nothing else in the state like Pioneer Days, she’s right. Find a Labor Day festival in Florida in its 63rd year that is so steeped in local history, involves so many people and organizations, boasts a parade that goes on for miles, and has so many activities that it takes three weekends to fit everything in.

We take for granted that every year there will be floats, pageants, contests, dances and cars, but do we really understand the amount of planning and man-hours that goes into making Pioneer Days happen every year?

 “Our job is to protect and preserve something that’s been standing in the community longer than anywhere else in Florida. We’re putting on a show. We want to deliver something to the community,” said Phelps, President of the Board of the Pioneer Days Committee. The Committee begins meeting regularly in May, but starts planning the year’s events months before that. 

Phelps has done the lion’s share of organizing Pioneer Days for years and this is her last term as president. Last year, after red tide forced the cancellation of the Michael O’Donnell Memorial Fishing Tournament and the relocation of the popular Cardboard Boat Festival, Phelps never imagined she’d be facing another major challenge this year. But in November, long-time Board member Steve Varga passed away suddenly. Varga not only handled the finances, but he also processed the parade applications and staged the parade, a mammoth undertaking. “He put every float into position. He knew the right order. He knew what people wanted to see,” said Phelps. “That’s a huge deal and it’s the one job I’ve never done.” 

Phelps worked so closely with Varga that she said she saw him as the person to take over for her next year. “It was really hard to lose him. He was a great friend,” she said. But just like last year when they battled red tide, and in 2016 when the Committee mourned the loss of Jean Airy, Phelps knew that nothing would stop Pioneer Days. 

In addition to losing her right-hand man, Phelps and the Committee lost funding from the Englewood CRA (Community Redevelopment Authority). Friends of Tiffany Square Bingo stepped in to lighten that loss, by donating proceeds from Sunday bingo this summer to help pay for expenses like barricades, restrooms, chair rental, permitting and more. Any money left after all the events goes to local charities. 

Most of the major events including the parade, festival, Chalkfest, car shows and Diaper Derby, remain in Sarasota County, but recent issues have led to Pioneer Days expanding more to the Charlotte County side of Englewood, and the County has proven to be a terrific partner. Last year, Charlotte County rescued the cardboard boat races after red tide chased the event out of its long-time home at Indian Mound Park. The move to the pool at Ann & Chuck Dever Regional Park was such a hit with the racers and the audience that the Committee voted unanimously to keep the race there this year. Charlotte County also donated the brand new recreation center at that park for the two school “Shipwreck” dances. “They were so accommodating to us,” said Phelps, who promises an even better experience at the races, with more shade and food trucks. 

In addition to the traditional events, new this year, Candace Stevens, owner of Wiseguys Barbershop and one of six candidates for Mayor for a Day, will have a booth at the festival to teach dads how to braid their daughters’ hair. Stevens, the mother of four daughters, said each dad/daughter will also receive a goodie bag. Pioneer Days Board member Dave McFadyen says, “This has the highest “Awwww” factor of anything we have done at Pioneer Days.”

Also new this year, if you can’t make it to the boat race or the parade, both events will be streamed live on the Pioneer Days YouTube channel. Phelps said that social media has become an increasingly important part of the festival and credits Jeannie Joyce, Karen Blackford and Sarah Garcia for their media savvy and getting the word out on Facebook, Instagram and other platforms. The organization is also proud of its website, where visitors can find out about events and entertainment, sign up for the parade, learn about the history of Pioneer Days and donate to the organization.

The website also provides the Committee with many of its volunteers. An online application details dozens of opportunities, from helping out at the Little Miss/Mr Englewood Pageant, to cleaning up after the festival. Volunteering just two hours makes a difference,” says Phelps “This is a committee of the community and we want people to be involved.”

For more information on Pioneer Days, to volunteer, see the photos in the annual Pioneer Days photo contest and much more, visit

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