- December 4, 2025
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Winter Garden Mayor John Rees spent time looking at dozens of covers of the West Orange Times & Observer from throughout the newspaper's history. The newspaper underwent 11 name changes in its 120-year history.
Members of Windermere High School's drumline rocked Observer sunglasses. The drumline went on to perform alongside drumlines from Ocoee, Horizon and West Orange high schools.
Observer Media Group's Leticia Silva, Amy Quesinberry Price, Madi Solomon, Sarah Santiago, Iggy Collazo and Megan Bruinsma (front) were thrilled to welcome hundreds of guests to celebrate the history and legacy of the West Orange Times & Observer.
Members of the West Orange Chamber of Commerce, including President and CEO Stephen Lewis, member Sonya Alvarez and Events and Sponsorship Manager Amy Pryor, came out in full force to celebrate the 120th anniversary of the West Orange Times & Observer.
Paige Winkler, Joe Berry and Lynn Wright looked over old editions of the newspaper throughout its history. "It's amazing," Wright said. "I grew up in Winter Garden. My grandfather was one of the founders. It takes me back."
Amy Quesinberry Price, the historian for the West Orange Times & Observer and Southwest Orange Observer, reunited with Andrew Bailey, the former publisher and co-owner of The West Orange Times.
Randy Rolfe, Shelly Rolfe, Whitney Laws and Brent Oravits with The Villages Daily Sun, which prints the West Orange Times & Observer and Southwest Orange Observer, joined the celebration.
Jim Zeitschel, a member of the West Orange Chamber of Commerce, was observed having fun at the West Orange Times & Observer's anniversary party.
Michael Eng, the editor and publisher, of the West Orange Times & Observer and the Southwest Orange Observer welcomed everyone to the anniversary party.
Emily Walsh, the president of Observer Media Group, smiled and waved to those who gathered to celebrate the West Orange Times & Observer's 120th anniversary. Observer Media Group purchased the West Orange Times in 2014.
Ocoee Mayor Rusty Johnson and Oakland Mayor Shane Taylor joined the festivities to celebrate the West Orange Times & Observer's 120th anniversary. They both enjoy reading the Ways We Were page each week in the newspaper.
Landra Wormack took a selfie with Cyndi Gustafson, Austin Arthur and Michael Eng.
Hundreds of community leaders and residents enjoyed a birthday party to celebrate the 120th anniversary of the West Orange Times & Observer, one of the oldest newspapers in the state.
The party took place Thursday, Sept. 11, at the Observer Media Group's Winter Garden office. West Orange Chamber of Commerce staff, including President and CEO Stephen Lewis, Carrie Acosta, Lynn Ramsey, Amy Cervantes and Amy Pryor; as well as ambassadors, including Sonya Alvarez, Jo Barsh, Pam Birdsong, Pat Brown, Monika Buyze, Loreta Delgado, Pat Gleason, Heather Easterling, Adam Markowitz, Kathleen Roat, Fr. Tom Rutherford, Chris Sapp, Laura Senzamici, Buss Woodley and Jim Zeitschel, all attended to mark the occasion.
Community leader Austin Arthur delivered a welcoming invocation.
Guests enjoyed refreshments courtesy of Pammie's Sammies, with catering by Gertrude's Kitchen. Observer historian Amy Quesinberry Price turned the office into a journalism museum, with a plethora of items used to report the news throughout the years. Guests also enjoyed perusing a variety of poster-sized front pages from throughout the paper's history and taking a peek at selected archives of the newspaper.
After a welcome by Editor and Publisher Michael Eng, the drumlines from Horizon, Ocoee, West Orange and Windermere high schools all performed — much to the delight of attendees.
The first edition of the newspaper, then known as the Winter Garden Ricochet, published on Sept. 13, 1905.
