- June 3, 2026
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Editor’s Note: The information presented in this article was taken from artifacts found in the Winter Garden Heritage Foundation and previous stories published in the West Orange Times.
Early settlers of Winter Garden nestled themselves among the groves of oranges trees and natural habitats the land had to offer. They spent their days farming in the fertile lands surrounding Lake Apopka as well as fishing and boating in its pristine waters.
When Winter Garden officially was established as a city in 1908, it didn’t take long for those settlers to look for other outlets to spend their free time. Soon, the baseball diamond made its way to the orange groves.
The sounds of baseballs cracking against the wooden bats soon filled the streets of the city and paved the way for recreational activities in the city we all know and love today.
Looking at the present day, baseball is a thriving sport in not only Winter Garden but also the greater West Orange community as a whole. The Winter Garden, Dr. Phillips, Windermere and Ocoee little leagues all serve as the youth’s first introduction to a bat and glove. Those introductory lessons translate to the players’ success in the dominant high school ball programs, including West Orange and Windermere high schools, The First Academy, and academies such as TNLX in Ocoee.
But before we truly can understand why there is an abundance of high-level Little Leaguers, high school players and the Winter Garden Squeeze, which is the community’s summer collegiate baseball team, we must first understand from where it evolved.
The Lake-Orange League, a semi-pro league that encompassed teams across Central Florida, found its way to Winter Garden’s sandlots in 1923.
George Walker, would serve as mayor of Winter Garden from 1933 to 1939, managed the hometown Winter Garden team in 1924 and also served as the director of the entire circuit. All his team’s early games were played on local sandlots in the community.
The Winter Garden team finished the 1929 season as runners-up, losing in the championship game 3-2 to Winter Park. At one point in history, Winter Garden and Ocoee baseball teams fused together for one season to form “Winteco.” The crossover likely occurred sometime during the 1930s or early 1940s.
“Directors and officers of the Lake-Orange Baseball League held a meeting at the Florida Power Corporation lounge Thursday night to study bylaws and regulations governing the operation of the forthcoming loop play,” the West Orange Times published in 1942. “This year’s play will be based on a 35-game play divided into two halves. Winner of the first half will meet the winner of the second half at the end of the season in the league’s ‘Little World Series.’ First half of play will (comprise) 21 games for each team, with the opening day set for Sunday, May 5. Eight teams — (from) Tavares, Mount Dora, Eustis, Winter Garden, Winter Park, Zellwood and Apopka — will form the league.”
Notable players for the league included Clifford R. Freeman, who became the mayor of Ocoee and an Orange County commissioner, and Vard Hager, who played for the league in the 1940s. Hager went on to play football, baseball and basketball for the University of Florida.
Once Walker became the mayor of Winter Garden, he worked toward raising funds to elevate the city. He secured funds from President Theodore Roosevelt’s New Deal to build projects such as the docks of Lake Apopka, a swimming pool and other facilities. But for baseball fans, his most important contribution from the $250,000 was developing Walker Field.
Those fields now house the Winter Garden Little League, Pop Warner football leagues and many other community events or leagues, but they first served as a venue for the 1930s players.
In 1936, the Albany Baseball Club trained at Walker Field as it was completed. In 1937, spring training in Winter Garden for the Baltimore Orioles International League began. Players from Rochester, New York, came down for the training.
Major League Baseball made its way to Winter Garden in 1942. For the first time in the history of the big league spring exhibition games, leaders in both the American and National Leagues played in the heart of Central Florida.
“President Clark Griffith of the Washington Senators called to attention today to Central Florida baseball fans a 12-game major league baseball schedule, representing the cream of the crop in both the American and National Leagues, which will open at Tinker Field, Orlando, Monday March 9,” the West Orange Times published in 1942. “For the first time in the history of big league spring exhibition games, leaders in both leagues will play in the heart of Central Florida. The schedule follows: New York Americans, March 9; Cleveland Americans, March 10; Detroit Americans, March 15; Brooklyn Nationals, March 17; St. Louis Americans, March 18; New York Nationals, March 19; Boston Americans, March 25; St. Louis Nationals, March 26; Boston Nationals, March 28; Cincinnati Nationals, March 31; Philadelphia Nationals, April 4 and 5. All games will be played at Tinker Field, Orlando, at 2:30 p.m.”
Those players stayed at the Edgewater Hotel.
Six years later, the Washington National Baseball School made its way to Walker Field and opened Jan. 28, 1948. The school welcomed 100 players on its opening day and 200 arrived by mid-week. The president of the school was Joe Engel, who also was the president of the Chattanooga Lookouts.
Engel was highly regarded in the baseball community, with a script of success in his past as a three-year, four-letter man at college and was given a fifth gold letter for the accomplishment. He wrote a letter dated back to Sept. 15, 1949, to Joe Pusateri of Ohio, reading:
“Trains run into Orlando, Florida, which is 12 miles east of Winter Garden. When you arrive on Jan. 4, go immediately to the Ball Park, where free sleeping quarters will be assigned to you. … Each student must furnish the following: your baseball uniform, shoes, glove and other personal equipment.”
In 1956, Alvin Berry attended the school and reported that it was $100 for the four weeks. He attended Jan. 4, to Feb. 1.
The baseball schools later closed in the 1950s and the MLB hasn’t returned to the Winter Garden area since. That was until the founding of the Winter Garden Squeeze in 2014.
The Winter Garden Squeeze is West Orange’s hometown summer collegiate baseball team in the Florida Collegiate Summer League. The Squeeze competes against six other FCSL teams, including the Leesburg Lightning, Sanford River Rats, DeLand Suns, Orlando Snappers and Winter Park Diamond Dawgs.
The FCSL is a nonprofit the MLB partially funds and was founded in 2003. It is one of 12 leagues in the National Alliance of College Summer Baseball. The Florida League gives college ball players the opportunity to play wood bat baseball against high-level opponents and prepare their future careers in professional baseball. It is regarded as one of the top summer leagues in the United States by Baseball America.
In 2014, the Squeeze posted a 23-20 record, placing third overall in its first season in the FCSL. General Manager Adam Bates started the franchise in honor of the deeply rooted history of baseball in Winter Garden. It’s an opportunity for local players and other Florida collegiate players to truly understand what it takes to play at the masters’ level.
Following the team’s inaugural season, the Squeeze has continued to find success within the dugout, aside from a temporary home field lapse in 2019 to 2021. The team returned to Winter Garden after overcoming COVID-19 and administrative changes, and played its home games at West Orange High in 2022.
In the Squeeze’s first year back at West Orange, the lineup recorded a 13-19 record, followed by a 17-17 record, 21-12, and most recently 13-20 in 2025. As the team prepares for its next season, slated with 25 games, it will branch out from its traditional blue and orange colors, and opt for purple and orange in honor of its second year at Horizon High.
The fresh lineup of 33 players includes some who have played for the Squeeze in the past and six players who call West Orange County their hometown. Its return marks a new opportunity for the collegiate baseball players to intertwine themselves deeper with the beloved sport of the area and provide an opportunity for the next generation of players to find their love for the game.
