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Turn back the wheels of time at the Pine Castle Pioneer Days

Pine Castle Pioneer Days is an annual family-friendly event to promote the living history of the Pine Castle area with demonstrations and educational activities, alongside food and craft vendors.


Step back in time at the Pine Castle Pioneer Days

This weekend local historians will turn the wheels of time backwards and share a piece of Central Florida history frozen in time within the Pine Castle neighborhood between Orlando and Kissimmee.


Pine Castle Pioneer Days takes place on Saturday, Feb. 24 and Sunday, Feb. 25, 2024 at Cypress Grove Park, 290 Holden Ave, Orlando. This free event features a recreation of the area’s turn-of-the-century events. Actors play out old dueling scenes and give history lessons, folk bands play, horse carriages give tours and vendors sell handcrafted wares.


This year’s Pioneer Days festival theme is “Wheels of Time,” which will delight antique and classic car, jeep and truck fans while teaching guests about Florida’s transportation roots.


This weekend's Pioneer Days will include amazing music, car shows, history, food trucks, games, craft vendors, lots of activities for children and a pie eating contest!


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Step back in time at the Pine Castle Pioneer Days

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