This week in West Orange County history

These are the people and events that helped create West Orange County.

  • West Orange Times & Observer
  • Neighborhood
  • Share


85 years ago

Used vehicles: 1931 Hudson sedan, $175; 1928 Essex sedan, $100; 1935 Austin panel truck, $250; Fordson tractor, $125; and 1931 Chrysler sedan, $175.

Miss Bessie Campbell and her brother, “Humpy,” returned from New Port Richey, where, with their mother, Mrs. A.L. Campbell, they had been the guests of Mr. and Mrs. Frank Britt.

Winter Garden was definitely pledged into the Lake-Orange Baseball League with games slated against Leesburg, Kissimmee, Mount Dora, Clermont, Apopka, Umatilla and Eustis. Merchants and businessmen pledged suits for the players.


80 years ago

The Winter Garden Flower Show attracted many visitors. The sweepstakes winner, Mrs. Harold Tilden, received a plant.

“Footloose,” the annual senior play, was presented. The roles were played by George Eby, Evelyn Stevens, Margaret Cappleman, Elmer Youngblood, Lydia Tilden, Lela Henderson, Wilson Griffith, Grace Brown and Aaron Moore. Proceeds from the play were designated for the gym fund.


70 years ago

E.M. Henderson was to take the office of postmaster in Winter Garden.  Mrs. J.S. Kirton was the retiring postmistress.


55 years ago

The new Winter Garden Inn sign signals the opening soon of Winter Garden’s finest motel and can be seen from either direction of Highway 50. It will advertise the city, as well as the motel and restaurant.


50 years ago

Windermere funnyman Winston K. Pendleton advertised his latest book, “2,121 Funny Stories and How to Tell Them,” for $5.95.

Helen Watson was slated to be the new principal of Tildenville Elementary School. She previously was the head of the Home Economics Department at Lakeview High and had been a teacher at Windermere Elementary.

Windermere resident Don Shaw was named principal at Hiawassee Elementary.



April 15, 1971

When Walt Disney World’s Magic Kingdom theme park was coming to town, The Winter Garden Times chronicled the development and construction every step of the way. The front page of the April 15, 1971, issue featured one of the first peeks at the Monorail train when the first section was lowered onto one of 337 concrete beams by handlers and technicians of the Martin-Marietta Company, which built the five-section trains.

The six trains were reported to be noiseless and run 45 mph on the 20-foot-high beams when taking guests to and from the 2,500-acre theme park, the Contemporary Resort-Hotel, the Polynesian Village and the Magnolia 18-hole golf courses.



This photograph taken on April 15, 1979, shows the construction of Winter Garden’s Municipal Complex, which included City Hall and the police department. In 2008, rapid growth necessitated the need for the larger structure that stands at 300 W. Plant St., although the police department still stands at the site.

The Winter Garden Heritage Foundation archive preserves thousands of photographs covering West Orange County’s history beginning in the 19th century. Call (407) 656-3244 to schedule a research appointment or to add to the collection.



Amy Quesinberry

Community Editor Amy Quesinberry was born at the old West Orange Memorial Hospital and raised in Winter Garden. Aside from earning her journalism degree from the University of Georgia, she hasn’t strayed too far from her hometown and her three-mile bubble. She grew up reading The Winter Garden Times and knew in the eighth grade she wanted to write for her community newspaper. She has been part of the writing and editing team since 1990.

Latest News