The spirit and stories of Florida’s earliest settlers came alive once again at the 33rd Annual Pioneer Day, held Saturday, November 8, at the Pioneer Village at Shingle Creek. Hosted by Osceola History, the free, family-friendly festival welcomed hundreds of visitors eager to step back in time and experience the rich pioneer heritage that helped shape Osceola County.
From the moment guests arrived, the grounds were filled with the sights, sounds, and aromas of “Old Florida.” Costumed interpreters and reenactors brought 19th-century life to vivid reality, showcasing traditional homesteads, Seminole camps, and hands-on demonstrations of blacksmithing, spinning, and candle making. Families explored the Village’s authentic historic buildings, gaining a deeper appreciation for the resilience and craftsmanship of Osceola’s earliest residents.
Live music set the tone for the celebration, while the Kids’ Craft Zone kept young visitors engaged with fun, history-inspired activities. The Pioneer Day Arts, Crafts & Market drew a steady crowd throughout the day, featuring handmade goods, home-baked treats, and unique creations from talented Florida artisans.
Osceola History’s annual event continues to grow as one of Central Florida’s most beloved community traditions — blending education, entertainment, and heritage into one unforgettable experience.
“Pioneer Day is about celebrating where we came from,” said an Osceola History representative. “It’s a day to honor the people who built this community and to share those stories with the next generation.”
Presented by Osceola History with support from Osceola County, Toho Water Authority, the City of Kissimmee, and Experience Kissimmee, this year’s event once again highlighted the community’s deep respect for local history and its commitment to preserving it for years to come.
For more information on upcoming Osceola History events and exhibits, visit OsceolaHistory.org or follow Osceola History on social media.
