Out-of-town visitors can enjoy an hour, a day, or even a week in Winter Park with the Scenic Boat Tour, Morse Museum of American Art, Polasek Museum, Rollins College, and a variety of shopping and dining on Park Avenue. Start at the Winter Park Historical Museum for a look at the founding of the city.

"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 from Loring Chase, 1881

Loring Chase was a Chicago businessman who came to Florida in February 1881 at the urging of his doctor to recover from chronic bronchitis. As his health would require wintering in a warm clime, he was encouraged to invest in Central Florida and toured what would become Winter Park. The South Florida Railroad ran from Sanford to Tampa, bending eastward through the area to accommodate the lumber trade of Capt. Coiner’s saw mill on the shores of Lake Virginia. Chase saw the potential of the ready transportation, high land, lush groves, and sparkling lakes, though only iron tracks, a wooden platform, and a few rustic homesteads existed at the time.

Chase contacted boyhood friend Oliver Chapman, who also happened to be in Florida, and the two men bought 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 central park. Chase and Chapman began selling lots and promoted the settlement throughout the Northeast.

The convenience of railroad service and the establishment of Rollins College in 1885 encouraged further growth. The commercial center extended along Park Avenue, while the Rollins campus developed along the shore of Lake Virginia to the south. Residences sprinkled the surrounding 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, Gen. Hannibal.

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. This is most apparent along Park Avenue.

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 Cape Canaveral 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.