- April 9, 2025
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Callie Valin, 6, felt like she was flying on the swings.
Colby Butler, 2, did not want to leave the bounce house.
Novalie Whaite and Ayah Topel loved the view from atop the Ferris wheel.
Holland Prillaman, 8, sat perfectly still at Family Church’s face-painting booth.
Windermere Mayor Jim O’Brien was the first victim in the dunk tank.
Handpicked performed a variety of classic bluegrass tunes.
Brandon and Jenna Smith zoomed down the potato-sack slide together.
Alyssa and Brooklyn Emmons conquered the giant potato-sack slide.
Florence Schiller, 9, shook the ball for good luck at the Roller Bowler game.
Armani Diaz had a blast running one of the many carnival games.
The Down Brothers band is a Windermere favorite.
Attendees enjoyed live music throughout the event.
Of course, no old-fashioned fair would be complete without a Ferris wheel.
Attendees were able to win tickets to claim some goodies at the prize booth.
Attendees loved donning some fun costumes for a few snapshot in The Van Cam.
Sawyer Brown entertained the crowd at the Windermere Centennial Fair with its repertoire of songs spanning 40 years.
Sawyer Brown entertained the crowd at the Windermere Centennial Fair with its repertoire of songs spanning 40 years.
The town of Windermere celebrated its 100th anniversary with a good old-fashioned fair last weekend.
The sold-out Windermere Centennial Country Fair took place Saturday, April 5, at The Pines at Windermere. Attendees enjoyed a full slate of live music, plus a huge selection of carnival games, rides and yes, plenty of prizes. A plethora of food trucks kept fair-goers satiated, as did the endless supply of popcorn and cotton candy. Some town officials and community leaders even took turns in a dunk tank — all to benefit the Windermere Police Department Foundation.
