
Englewood’s Labor Day tradition is back on track for 2024. In 1956 Jo Cortes, local journalist and community activist, came up with the idea of “Pioneer Days.” The purpose was to celebrate the 60th anniversary of the founding of Englewood and to honor local pioneers. Today plans are in motion to finalize plans for the upcoming Pioneer Days Labor Day Parade.
Pioneer Days has faced several challenges in recent years, with events canceled due to red tide, COVID-19, and road construction on West Dearborn Street. In 2023, only a few traditional events were organized, with a parade and festival quickly assembled.
This year, Pioneer Days aims to revive more traditions, including the popular cardboard boat races, the Mayor 4 a Day contest, and a party at Pioneer Plaza featuring food, drinks, and possibly vendors.
The cardboard boat races are scheduled to kick off at 10 a.m. on August 31 at Indian Mound Park. The Englewood Sailing Association, in partnership with Lasbury Tracy Realty and St. David’s Jubilee Center, is organizing the event. Cardboard boat building clinics will be held from 9 a.m. to noon on August 24 and 25 at Indian Mound Park, with a hot dog lunch provided. “Cardboard will be supplied,” said Doug Izzo, Executive Director of the Englewood Chamber of Commerce. He also mentioned that boats can be stored at Indian Mound Park until race day. To register a boat, visit englewoodchamber.com and access the community event calendar.
The Labor Day parade is tentatively set for 9 a.m. on September 2 along West Dearborn Street. Parade staging will take place at the plaza near Obee’s Subs at 240 S. Indiana Ave., with early arrival encouraged for setup. “Anyone can join the parade,” Izzo said, emphasizing that it’s a free community event. The application form is available on the chamber’s website.
Judges will be stationed at the Hesse family lot on West Dearborn. The parade will feature floats, the Lemon Bay High School Marching Manta Band, color guard, Bit of Hope Ranch horses, and more. The grand marshal, a person recognized for significant community contributions, will lead the parade. The Mayor 4 a Day will represent a nonprofit, campaigning and raising funds for their chosen cause. Amy Gonzales is chairing the Mayor 4 a Day committee, with candidates including Iris Beaugrand of Fandango Sanctuary, Laura Roy of St. David’s Jubilee Center, and English Jan of Angel Land Food Forest.
Debates among the candidates are scheduled for:
• 5:30 p.m. on August 7 at American Legion Post 113, 3436 Indiana Road
• 5:30 p.m. on August 15 at The Waverly Restaurant, 2095 N. Beach Road
• 5:30 p.m. on August 20 at the Englewood Elks Lodge 2378, 401 N. Indiana Ave.
Post-parade activities at Pioneer Park are still being planned, but attendees can anticipate a pie-eating contest, entertainment, a Diaper Derby, and plenty of food. This year’s theme, “Happy Days Are Here Again: 1950s Revival,” marks a return to the original spirit of Pioneer Days.
Those interested in volunteering can contact Doug Izzo at [email protected].

