The annual Pioneer Day celebrates Osceola County’s first residents and the pioneering spirit of the late 19th century. Step back in time at this annual festival hosted at the Pioneer Village at Shingle Creek in Kissimmee.

Pioneer Day is a free, family-friendly event featuring live music, a kids’ craft zone, a real Florida Market, and pioneer and Seminole life demonstrations. As visitors explore the Pioneer Village they will learn how Florida Seminoles and early pioneer families lived off the land long before electricity and air conditioning. 

Sandy Back Porch performed at the 2019 Pioneer Day festival.

Pioneer Day Art, Crafts & Market

Purchase unique art, crafts, and food products from talented Florida residents. Great options for seasonal and holiday gifts! Delicious homemade baked goods for sale too. There’s something for everybody at the Pioneer Day Art, Crafts & Market.  

For more information on signing up to be a Pioneer Day Market Exhibitor please email 
*Non-refundable fees do apply. 

This event is sponsored in part by Experience Kissimmee.
For visitor information visit