1925-1935
The Pavilion
At the end of Oakland Ave, a dock and pavilion were built, complete with a slide from the second story. Bathing at the Pavilion cost just 10 cents, and it also became a popular spot for picnics.
Ocoee Hotels
A wooden hotel, known as the Ocoee Hotel, was built on the south side of McKey St, nestled between Bluford and Cumberland Ave. The hotel featured 9 rooms and a cozy parlor for guests to enjoy. The Ocoee Inn was also a happening place with a popular restaurant for dining and special occasions.
Ocoee High School
In 1926, Ocoee High School boys' basketball & baseball teams went to the state championship games but sadly, both teams lost.
The Cardinals
In the 1930s, the St. Louis Cardinals' farm team held their Spring training in the area, and it became known that they were getting new uniforms. Their old uniforms were donated to Ocoee High School, which led the school to adopt the Cardinal as its mascot and choose red and white as its colors. Today, in 2025, the Cardinal remains the mascot for both Ocoee Elementary and Middle schools, and red and white continue to represent our school spirit!
1935-1945
Works Progress Administration
In 1936, President Roosevelt established several government programs to help recover from the Great Depression, one of which was the Works Progress Administration (WPA). The trustees of Ocoee requested funding from this program and were granted it, leading to the construction of one of the first two gymnasiums in Orange County—one in Orlando and the other in Ocoee.
Trade School
In 1939, a trade school opened at Ocoee High School which was only 1 of 3 trade schools in the state of Florida. The attendance grew to 300 students and taught trades like auto mechanics, welding, airplane mechanics, carpentry, painting, & more!
1945-1955
Halloween Carnival
During this decade, the Ocoee Halloween Carnival was a very popular event that took place every year in downtown and was hosted by the Ocoee PTA.
Ocoee's First Fire Chief
From 1946-1955, Harold Douglas Maguire was Fire Chief of the first organized Fire Department in Ocoee. He, along with Walker Creel, built a fire truck for Ocoee. During the early 1950's, he served as Police Chief for the City of Ocoee. Elected to the Ocoee City Council in 1955, he became Mayor in 1956 and served two years in office, not seeking reelection.
1955-1965
SR 50
State Road 50 (SR 50) was constructed south of downtown Ocoee in 1959 and provided a direct east-west connection between the City and a growing Orlando. The development of SR 50 made Ocoee more accessible and attractive to developers, who wanted to build new affordable housing developments.
Florida's Turnpike
Florida’s Turnpike was the next major roadway constructed through Ocoee. This 309 mile long freeway was extended through West Orange County in 1964, just south of the Ocoee downtown area, and provided Ocoee with excellent north-south access.
1965-1975
Birth of Maguire Airport
During this decade, Maguire Airport became an official airport and was a key local hub for the Central Florida community. It was owned and operated by Harold Douglas Maguire until the 1970s, when his son, Harold Douglas Jr., also known as Mickey, took over. Tragically, Mickey was killed in an aviation accident in January 1972.
Colony Plaza
The Colony Plaza, formerly the Ramada Inn, was leased by Disney and people were not allowed inside unless their name was on a special list. After years of its existence, The Colony Plaza was a hot spot in Ocoee for people to come and hang out, and have a drink by the bar.
Ocoee H.S. State Champs
In 1973, the Ocoee High School baseball team won the State Championship title and were lead by head coach - Gary Guthrie.
1975-1985
50 Years of Ocoee High School
In 1975, Ocoee High School celebrated 50 years of existence. In that same year, West Orange High School was built.
Ocoee's 60th Anniversary
The city celebrated its 60th anniversary in May of 1985 with activities including a street party, parade, festival and dinner for all residents who had lived in the city for 60 or more years.
1985-1995
My Girl
The famous movie "My Girl" bingo scene was filmed in Ocoee at the Ocoee Christian Church on the corner of Bluford just south of McKey St. This movie went on to become a classic and left a great memory for our beautiful city!
Health Central Hospital
The hospital opened in 1994 employing 300-500 professionals and support staff.
1995-2005
West Oaks Mall
The West Oaks Mall was built in 1996 and created many jobs that helped the economy to be more localized instead of having to travel out of town.
Ocoee High School
In 2005, the new Ocoee High School was built in Ocoee.
2005-2015
Tom Ison Center
In August of 2006, the Tom Ison Veteran and Senior Center had its grand opening!
Colony Plaza Implosion
The Colony Plaza Hotel, formerly the Ramada Inn, was leased by Walt Disney World, the landmark hotel contained a lounge, swimming pool, tennis courts, and meeting rooms. It was also the first hotel in Orange County to receive a license to serve liquor with meals on Sunday. In 2009, the Colony Plaza was in a severe decline so it was condemned by city officials for code violations. By 7:15 am on the morning of May 9th, the building was imploded and turned to dust.
The Whisper Home
In 2010, Producer Jerry Eisinger's movie "The Whisper Home" was filmed in Ocoee. This movie went on to be featured in three different movie festivals and was nominated "best screenplay" at the Phoenix International Christian Film Festival.
2015-2025
Commissioner George Oliver 111
In 2018, history was made when George Oliver III was appointed as the first African American Commissioner for the City of Ocoee.
First Female Police Chief
In 2021, Ocoee made a groundbreaking move by appointing Saima Plasencia as the city’s first female Police Chief, marking a significant achievement for our community!
New City Hall
In 2022, Ocoee underwent a transformation with the construction of a new City Hall, featuring modern resources that supported the city's continued growth and development.
Chief Vincent L. Ogburn Sr.
In 2024, Ocoee made history with the swearing-in of its first African American Police Chief, marking a significant milestone for our city!
Unity Park
In 2024, the City of Ocoee unveiled a memorial to honor the lives lost and the homes destroyed during the 1920 Ocoee Massacre, paying tribute to the African American community affected by this tragic event.