Winter Park History

Our city traces its founding to Loring Chase, who visited Florida in 1881. Mr. Chase was a Chicago businessman who suffered from chronic bronchitis and was urged by his doctor to winter in a warm climate.

While in Florida, he was encouraged to visit the central part of the state and tour what would become Winter Park. Though only rail tracks and a few rustic homes existed at the time, Chase saw the potential of ready transportation, high land, lush groves and sparkling lakes of the region we now call Winter Park.

“As we rode along the lovely shores of Lake Virginia, Osceola and Maitland I was delighted, and having been in the real estate business for many years, had an eye for town sites and built not a castle in the air but a town, never thinking it would materialize.”

— Letter to a friend from Loring Chase, 1881

Original Winter Park Settlement

Original Winter Park Settlement

Excited about his vision of a community, Chase contacted boyhood friend Oliver Chapman and the two men purchased 600 acres of land around the shores of several lakes for $13,000. They hired surveyor Samuel A. Robinson of Orlando to lay out a tidy grid of residential streets with curves encircling sites designated for hotels, schools, churches, and a large central park in the downtown district.

The convenience of railroad service and the establishment of Rollins College in 1885 encouraged further growth of the community. The commercial center extended along Park Avenue, while the Rollins campus developed along the shore of Lake Virginia and to the south residences began on the new streets and lake shores. The west side of the new town was designated as a community for African Americans and named Hannibal Square after the ancient Carthaginian, General Hannibal.  Chase and Chapman began selling lots by promoting the settlement throughout the Northeast.

The beautiful little town attracted winter visitors and gained a reputation as an art and literary colony. Citrus emerged as a mainstay of the economy, which slowed in the mid-1890s following devastating freezes. Early in the 20th century, prominent northern businessmen invested, once again sparking the Florida Land Boom. This spurred the bricking of streets, the opening of new subdivisions, commercial buildings and schools.

The collapse of the Boom in the late 1920s dampened construction activity, which remained slow through the early years of the Great Depression. Winter Park rebounded in the late 1930s, and economic development resumed with renewed intensity after World War II. Development since 1950, stimulated by the establishment of Kennedy Space Center, Disney World and the emergence of Orlando as a regional banking service center, has resulted in the loss of many historic buildings to the demands of growth. Nevertheless, Winter Park retains a number of buildings from its early years.

Winter Park Sidewalk Art Festival

Winter Park Sidewalk Art Festival

Today visitors can still enjoy the art-colony aspect of Winter Park when they visit the world’s largest collection of Tiffany glass at the Morse Museum of American Art, the beautiful sculptures at the Polasek Museum, and the exciting exhibits at the Cornell Fine Arts Museum located at Rollins College. The beautiful lakes and residences are best viewed from aboard the Scenic Boat Tour as it motors through the lakes and connecting canals of the city. In addition, Central Florida’s finest shopping and dining is located along Park Avenue and can be enjoyed as you stroll along Central Park, still the centerpiece of our town.

United Arts of Central Florida  |  Florida Arts and Culture : Division of Cultural Affairs City of Winter Park, FloridaCultural Affairs