Englewood’s Pioneer Days Returns for Labor Day Weekend
ENGLEWOOD — Englewood is gearing up to honor its history and community spirit with the annual Pioneer Days celebration, running over Labor Day Weekend. The long-standing tradition brings together families, local organizations, and visitors for parades, contests, and festivities highlighting Englewood’s pioneer heritage.
This year’s schedule includes:
Little Miss/Mr. Englewood Pageant
9 a.m.–noon, Aug. 23, Englewood Skye Academy, 871 S. River Road
Girls up to 12 years old and boys up to 6 years old will compete in this community favorite. Contestants can still register the morning of the event with cash payment of the $30 entry fee. Proceeds benefit the Englewood YMCA. Doors open at 8 a.m., and admission is free.Mayor 4 a Day Reveal
6 p.m., Aug. 29, Landy’s Restaurant, 1400 Aqua View Lane
The honorary title of “Mayor for a Day” will be announced during this evening gathering.Cardboard Boat Races
10 a.m., Aug. 30, Indian Mound Park, 210 Winson Ave.
Homemade cardboard boats will compete on the water in this unique event. Registration closes at 5 p.m. on Aug. 28. A special “boat giveaway” will be held Aug. 23 at The Sailing Center, where participants can claim a boat with a refundable $25 deposit. Food, drinks, and live music will also be available.Pioneer Days Parade
9 a.m., Sept. 1
This year’s parade theme is “Englewood History.” The procession begins at Obee’s parking lot, 240 S. Indiana Ave., then travels along West Cowles Street, north on McCall Road, and west down Dearborn Street, ending at Veterans Memorial Pavilion. Entry deadline is Aug. 28 at 5 p.m. The 2025 grand marshal is Nancy Wille, a long-time member of the Lemon Bay Historical Society and recipient of the group’s 2023 Legacy Award. Wille was also inducted into the Secret Society of Smoked Mullets in 2021. WENG Radio will broadcast the parade live.Pioneer Days Festival
10 a.m.–2 p.m., Sept. 1, Pioneer Plaza, 325 W. Dearborn St.
Following the parade, the festival will feature live music, contests including watermelon, pie-eating, and beard competitions, children’s activities, food vendors, and the announcement of parade winners.
Additional events, including the Diaper Derby and gatherings at the Lemon Bay Woman’s Club’s historic clubhouse, round out the weekend’s activities.
For more details, registration forms, or event information, visit www.englewoodchamber.com/pioneer.