Osceola History invites the community to celebrate the spirit and stories of Florida’s earliest settlers during the 33rd Annual Pioneer Day, taking place Saturday, November 8 from 10 a.m. to 4 p.m. at the Pioneer Village at Shingle Creek, located at 2491 Babb Road in Kissimmee.
This free, family-friendly festival honors Osceola County’s rich pioneer heritage and the resilience of its 19th-century residents. Visitors can explore the historic Pioneer Village, where authentic structures and costumed interpreters bring history to life — from traditional pioneer homesteads to Seminole camps, offering an immersive glimpse into Florida’s past.
Guests will enjoy live music, a kids’ craft zone, a real Florida market, and captivating demonstrations showcasing pioneer skills and Seminole traditions.
Pioneer Day Arts, Crafts & Market
The event’s lively market will feature an array of handmade arts, crafts, and food products from talented Florida artisans. Visitors can also pick up delicious homemade baked goods and one-of-a-kind creations while supporting local makers.
With free entry and free parking, Pioneer Day is the perfect opportunity for families, history enthusiasts, and visitors to experience “Old Florida” while celebrating the people who shaped Osceola County’s earliest communities.
Pioneer Day is proudly presented by Osceola History, with support from Osceola County, Toho Water Authority, the City of Kissimmee, and Experience Kissimmee.
For more information, visit OsceolaHistory.org or follow Osceola History on social media for event updates.
