2025 Year in Photos: September

Thousands of West Orange residents honored the life and legacy of Charlie Kirk at a vigil held Saturday, Sept. 20, on the steps of Winter Garden City Hall.

Southwest Orange’s celebrity horse, Tsaber, will turn 38 this month, and locals celebrated him at a birthday party Sept. 13.

Andy Williams, a fifth-generation Windermere resident, and his mother, Lavina Williams, sit on the front porch of her home on Lake Down. All of the photos they are holding were taken on the same porch.

West Orange Times & Observer celebrated its 120th anniversary with a party Sept. 11, 2025.

The Winter Garden Cracker Barrel was one of only four restaurants nationwide that was renovated with a new look and logo.

Windermere Mayor Jim O’Brien, Orange County Mayor Jerry Demings, Oakland Mayor Shane Taylor, Ocoee Mayor Rusty Johnson and Winter Garden Mayor John Rees shared their thoughts at the West Orange Chamber of Commerce’s State of the County Q&A.

Home State Brewing Co. held its annual Oktoberfest with live music, games, food and beer.

Windermere Preparatory School celebrated its 25th anniversary in 2025.

Mayra Feliciano, from Dr. Phillips High School’s Air Force JROTC program, was recognized as the No. 1 cadet in the world.

The Winter Garden Heritage Foundation and Opera Orlando joined forces to present “All is Calm: The Christmas Truce of 1914,” in December.

It’s all in the family for Debbie Cappleman, Larry Cappleman, Holt Cappleman and Jennifer Cappleman as they work together to maintain the legacy of Urban on Plant Kitchen & Bar while adding to the family’s legacy on Plant Street.

Artist Jordan Emmitt created a new mural that transformed Westbrooke Elementary’s media center.