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Osceola Pioneer Days

November 3 - November 4

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.

November 3rd is dedicated to local schools who tour the grounds and interact with the various living historians. Last year, The East Florida Rangers participated. While the event is not in EFR’s time, rangers used the opportunity to discuss the early history of Florida and how, after the end of the Revolutionary War, many people moved inland. This generated great conflicts over land during what is known as the Seminole Wars period.

Saturday, November 4th, 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.

Bob Samson has agreed to be the docent at the church on-site during the event.

We have a nice group of rangers already committed to attending both days. If you cannot make both days, come Saturday. Katie Dile has volunteered to provide meals for both days. Setup is Thursday afternoon and teardown is Saturday after 4 pm.

You must complete your application by October 29th to be considered for the November Pioneer Day event. If you have any questions, please email volunteer@osceolahistory.org.

The Pioneer Park’s history and docent manual can be downloaded here.

Registration form here.




November 3
November 4
Event Category:


Submitter's Name
Bob Samson
Submitter's Email


Pioneer Village at Shingle Creek
2491 Babb Rd
Kissimmee, FL 34742-1996 United States
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(407) 427-9692
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