July 29, 2026
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Groovy Ballots and Bell-Bottoms: Englewood’s 70th Pioneer Days Pairs a Disco Parade with the ‘Mayor for a Day’ Race

Englewood’s Pioneer Days

Can you feel the excitement in the air? Pioneer Days are almost here! This year marks the 70th anniversary of Englewood’s cherished tradition, and Englewood is turning back the clock with a “70s Disco” theme for the parade. Break out your bell-bottoms and sequins because it’s going to get groovy.

Pioneer Day Parade

Englewood Pioneer Days happens every Labor Day Weekend. To get you ready, the Englewood REVIEW comes out August 28th with our special Pioneer Days edition, packed with all the details you need. 

Here are just a few of the fun and fabulous events to look forward to:

– Little Miss/Mr. Englewood Pageant
– The wild Cardboard Boat Races
– Diaper Derby (as competitive as it sounds!
– The iconic parade down Dearborn Street
– Family fun at Pioneer Plaza

The competitive Diaper Derby

Let’s talk about the “Mayor for a Day” candidates; always a crowd favorite

This year’s hopefuls:

– Courtney Defilippis representing The Literacy Center (TLC)
– Todd Dunn for EFD Firefighters Benevolent Fund
– Kris Hartley (with her dog, Shea) for Suncoast Humane Society
– Karen Harvey for Englewood Helping Hand
– Victoria Macri for Operation Healing Heroes Foundation

Each candidate is organizing their own fundraising events, leading up to all the Pioneer Days festivities. The Mayor for a Day will ride in the parade, wear the sash, and help show off all the things that make Englewood great.

The wild Cardboard Boat Races

This year’s committee chair is Mike Dalke, working with Mary Jones and Amy Gonzales to pull it all together. Over the years, money raised at this event has lifted up many local charities, some of them completely new to the spotlight. It’s a chance to make a real difference while having a great time.

If you have questions or want to get involved, reach out to Amy at 360-431-6910. Fundraising kicks off on August 1st. Thanks to the Englewood Chamber for making this all happen for the community. Let’s celebrate 70 years together!

Click here for more information.

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