Englewood Pioneer Days will return over Labor Day weekend and the week prior with a full schedule of festivities, including pageants, a parade, races, and contests.
Events begin with the Little Miss/Mr. Englewood Pageant on Saturday, August 23 and concludes on Monday, Sept. 1 with the Pioneer Day Parade and activities at Pioneer Park.
Youth Pageants Open the Week
The Little Miss/Mr. Englewood Pageant will take place Saturday, Aug. 23, from 9 a.m. to 12 p.m. at Englewood Methodist Church, 700 E. Dearborn Street. The event is open to boys and girls ages 0 to 12.
The Miss Englewood Pageant, for girls ages 15 to 18, is scheduled for Saturday, Aug. 30, from 5 p.m. to 8 p.m., with the location to be announced.
Applications and details for both events are available at www.englewoodchamber.com/pioneer.
Cardboard Boat Races at Indian Mound Park
The Cardboard Boat Races will be held Saturday, Aug. 30, beginning at 10 a.m. at Indian Mound Park. Organized by the Englewood Sailing Association, Lasbury Tracy Realty, and St. David’s Jubilee Center, the event invites participants to race homemade cardboard boats in multiple heats. Food and drinks will be sold on-site.
Visit www.englewoodchamber.com/pioneer for registration forms.
Parade and Public Activities on Sept. 1
The Pioneer Day Parade begins at 9 a.m. on Monday, Sept. 1. The parade will stage at 240 S. Indiana Avenue and travel from the Obee’s parking lot down W. Cowels Street, turning onto McCall Road and ending on Dearborn Street at the Veterans Memorial Pavilion.
Visit www.englewoodchamber.com/pioneer for paraderegistration forms.
After the parade, activities at Pioneer Park (325 W. Dearborn Street) will begin around 10 a.m. The schedule includes:
- 10:20 a.m. – Parade Winners Announced (Englewood Chamber)
- 10:30 a.m. – Diaper Derby (Lemon Bay Woman’s Club)
- 11:00 a.m., 12:00 p.m., 1:30 p.m. – Live Music (Dale Shumate)
- 11:30 a.m. – Pie Eating Contest (Dearborn Coffeehouse)
- 12:30 p.m. – Watermelon Eating Contest
- 1:00 p.m. – Beard Contest (Sydney Martin)
Games and Booths at Pioneer Plaza
From 10 a.m. to 1 p.m., Pioneer Plaza will host games and booths from local organizations, including:
- GFWC Rotonda Woman’s Club
- Englewood Family YMCA
- Prop It Up Photo Booths
- Englewood History Museum
- Englewood Amateur Radio Society
Additional participants include the Low Rider Dachshund Foundation (dog treats), Grace Community Church (snacks and water), and the Englewood Chamber of Commerce (community information). Vendor applications remain open.
Visit www.englewoodchamber.com/pioneer for vendor applications.
Beard Contest Set for Afternoon
The Beard Contest begins at 1:00 p.m. All ages may enter. Prizes and recognition will be given for the longest and most distinctive beards. Visit www.englewoodchamber.com/pioneer for beard contest applications.
Parade Leadership and Mayoral Candidates
The 2025 Grand Marshal selections and Mayor candidates are still to be announced. Mayoral candidates will raise money for selected charities, participate in the parade, and attend event functions.
Committee chair Jeannie Joyce, with members Mike Dalke and Cyndi Fredricks, encourages participation. “All the charities win,” Joyce said. “They keep what they raise and gain exposure.” For more information, contact Joyce at 360-431-6910.
Applications, forms, and more event updates are available through the Englewood Chamber and the Englewood Pioneer Days website: www.englewoodchamber.com/pioneer.
