The 31st Annual Pioneer Day was held on Saturday, November 4, 2023.

  • 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. 

Pioneer Day Art, Crafts and Market

Purchase unique art, crafts, and food products from talented Florida residents. 

  • Purchase unique art, crafts, and food products from talented Florida residents. 
  • Delicious homemade baked goods for sale too.
  • There’s something for everybody at the Pioneer Day Art, Crafts & Market! 
Pioneer Day photo collage - decorative

Pioneer Day Volunteers

Join us for a day of fun by volunteering at our annual Pioneer Day. If you or your community group are interested in volunteering for set up and tear down of the event, joining us by dressing in Pioneer attire and running kids’ activities or interpreting historical buildings, please complete the volunteer application.

Volunteers do require training so please complete your application by October 29th to be considered for our November Pioneer Day event. If you have any questions, please email volunteer@stuartw54.sg-host.com.

For the comfort and safety of our guests as well as the historical significance of our structures, please always observe the following guidelines when attending Pioneer Day:

  • No pets (other than registered service animals)
  • No smoking or vaping on site
  • No bicycles
  • No skateboards
  • No motorized vehicles

2023 Event sponsors:

Sponsored by:

Osceola County Florida logo
Kissimmee City logo updated
Toho Water Authority logo
KUA logo
Florida Arts and Culture tall
Experience Kissimmee Logo