Windermere spending year celebrating 100th anniversary

West Orange Times & Observer
News

It was a century ago that Cal Palmer, J. Howard Johnson and Howard Lyon — three men from Ohio who had fallen in love with the area’s clean lakes, lush orange groves and fine timber stands — incorporated the town of Windermere.

To commemorate the 100th anniversary of the founding of the town of Windermere, officials are spending the next year celebrating the 2.2-square-mile town’s achievements and paying tribute to the town’s past.

The Centennial Planning Committee has been working diligently to plan a year of exciting events and activities to recognize the milestone. Many projects are taking place this year as well.

HISTORY OF WINDERMERE

The area known now as Windermere was home to the Timucua Indians until the 1500s, when Spanish settlers moved in. In 1821, the eastern half of the state was purchased from Spain by the United States, and by 1845 Florida was the 27th state welcomed into America.

The U.S. Government offered incentives to bring more people to this area and gave away 160 acres of land to any person willing to cultivate five acres. Settlers found their way to Windermere, followed by railroads, steamboats and tourism.

John Dawe, one of the first English settlers, laid out the town in 1887, and it is believed he named the town after Lake Windermere in England.

In 1925, Windermere, Florida, was incorporated by Cal Palmer, J. Howard Johnson and Howard Lyon. John Jaquith served as the town’s first mayor. Palmer was the town’s second mayor; Johnson, its fifth; and Lyon, its seventh.

In just five years, the town’s population grew to 153 residents. By 1960, the population had increased to 596 residents, with a significant increase coming in the late 1950s thanks to Martin Corp employees moving into Central Florida.

Up until the late 1960s, there was only a single marshal in charge of town safety. In 1968, Windermere named Bill Bozette its first police chief. The police department had just one other officer.

In the early 1970s, an influx of California executives with Walt Disney World moved to Windermere. By the early ’80s, Windermere had a population of more than 1,200 residents. With the expansion of the Walt Disney Resort and the booming cityscape of Orlando, that number has grown to more than 3,500.

Three buildings in the town of Windermere have been added to the National Register of Historic Places, which protects the memory of the foundation of the town:

• Town Hall, 520 Main St., began as the Woman’s Club. Construction was completed in 1924.

• Cal Palmer’s office building was constructed in 1911 at 502 Main St. and still stands today.

• The Historic 1890 Windermere School House, now known as the Parramore House, was the first school in Windermere. This single-story wooden structure, built in 1890, gives a glimpse into the past and what education was like for early settlers living in a rural section of Florida. It is one of the last historic buildings that remain from that era. It was used as a schoolhouse until 1916 and then served as a civic club and Woman’s Club gathering place.

Committee member CT Allen said the goal was to create projects that would get residents involved and would last long after the centennial celebration was over.

“Every project we took on we wanted it to be a lasting footprint for the town,” she said. “We want to do something special for the town people, and we also want to do something for the local community.”

To kick off the celebration, the Windermere Town Administration building offers a historical photo slideshow and history in the new Centennial Lobby. More than 300 old photographs of the town and its residents are accompanied by an oral history recorded by Windermere residents. Four commissioned oil paintings, on loan from longtime resident John Nabors, are on display and depict historical buildings that are an integral part of the town’s heritage.

Residents also will be able to purchase centennial merchandise in the lobby.

For 2025, the town has been given a festive makeover, including celebratory centennial banners on the light poles and three centennial entry signs, to greet Windermere residents and visitors.

The Parks and Recreation Department launched a centennial bench project in which residents can purchase a metal park bench that includes a donation plaque. These benches will replace old ones throughout the town. Benches still can be purchased by visiting town.windermere.fl.us/centennial-celebration.

MAJOR CELEBRATIONS

The committee has planned two big celebrations — in addition to a number of smaller events throughout the year.

“It’s going to be a fun time,” said committee member Gregg Anderson. “We have so much history in this town. A lot of legacy families, a lot of great of old photographs.”

The first event is the Lighting of the Centennial Flames at 6 p.m. Friday, Jan. 24, in front of Windermere Town Hall. Two gas lamps will be lighted by a centennial torch held by Windermere Mayor Jim O’Brien and Palmer Luff, a grandson and one of the last descendants of town founder Cal Palmer.

“It will be a symbol of light for the next 100 years,” Allen said.

Both O’Brien and Luff will speak at the ceremony, to which dignitaries and VIPs have been invited.

“As mayor, I am excited to kick off the town of Windermere Centennial Celebrations on Jan. 24,” O’Brien said. “The lighting of the ceremonial torches will mark the official opening of the town’s centennial celebrations. I am most proud of our Centennial Planning Committee’s work — many of our events will reach to our past and leave a lasting legacy for both our town and the West Orange community.”

Jan. 24 also is Food Truck Night in Windermere.

The second big event is the Centennial Country Fair, scheduled from noon to 7 p.m. Saturday, April 5, at the Pines at Windermere. The day will include carnival games, rides, food trucks and music. The fair will culminate with a concert by a popular country band.

Tickets are not yet on sale, and the committee hasn’t determined pricing, but they will be available through the town’s website. Anderson said tickets will be priced affordably for families to enjoy a full day of fun.

“We can dress in goofy clothes and talk about the way things used to be,” Anderson said. “It will be just hokey enough to be a lot of fun.”

YEARLONG CELEBRATIONS

The first centennial-inspired event was last weekend when the Rotary Club of Windermere hosted its annual Lobster and Laughs event at The Pines of Windermere.

The next event is the Windermere Tree Board’s tree give-away from 9 a.m. to noon Saturday, Jan. 18. There are two categories this year. In the standard give-away, each household can receive one free tree to be planted anywhere on the property. In the Centennial Celebration Legacy Tree Give-away, these special designated trees have the potential to live at least 100 years and must be planted in front yards where they can be viewed by folks passing by. Once they are planted, they will receive a metal marker designating them as Centennial Celebration trees. Visit the town website for information on registering.

The annual Windermere Wine & Dine is Saturday, Feb. 1, and ticket-holders are treated to an evening of wine, light bites and live music.

The Art Room is hosting several events. A student art show featuring the centennial theme takes place March 1. Younger children can participate in a Mom and Me activity by drawing or painting the old schoolhouse April 6. Older children can paint their version of Town Hall April 13. Adults can take part in the Art Makes Me Happy series April 25 with a general focus on Windermere, whether it be a park, Bird Island, the old gas station or post office, or any other town element. Registration is through The Art Room.

On July 4, the town will host its annual Fourth of July Pancake Breakfast at Town Hall for Windermere residents.

After taking the summer off, the town is hosting the annual Run Among the Lakes Oct. 11.

The Windermere Police Department Foundation is putting together bunk beds for needy children through the Sleep in Heavenly Peace project Oct. 18.

Beer Fest will take place Oct. 25 with craft beers and beer-related activities in conjunction with Windermere Brewing Company.

The holiday season will kick off Nov. 21 with the traditional Light Up Windermere event.

The centennial year wraps up with the Movie in the Park and visits with Santa Claus.

Allen said town committees and boards could add smaller events to the calendar throughout the year.

“I look forward to seeing all of our residents participate in highlighting the town of Windermere’s past, present and future as a community that protects small-town values and remains a great place to raise a family ‘Among the Lakes,’” O’Brien said.

author

Amy Quesinberry Price

Community Editor Amy Quesinberry Price 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.