The history of Winter Park, Florida, is a tapestry of visionaries, milestones, and community spirit. The roots of this remarkable town date back to 1858, when David Mizell Jr. and his family became the first settlers, establishing a homestead near Lakes Virginia, Mizell, and Berry. The small settlement, initially known as Lake View and later renamed Osceola in 1870, grew around the homestead, laying the foundation for what would become Winter Park.

The area's transformation gained momentum in the 1880s. Loring A. Chase (1839–1906), captivated by the lush landscapes and balmy climate, visited the region in February 1881. Partnering with his lifelong friend Oliver Everett Chapman (1851–1936), Chase purchased 600 acres of land for $13,000. Together, they envisioned a residential retreat for wealthy Northerners, complete with a grid of streets, a 10-acre central park, a lakeside resort, and a residential area for domestic and grove workers. By late summer of 1881, they had formally laid out their vision and named it Winter Park.

In March 1882, Winter Park’s first railroad depot was completed, connecting it to the burgeoning South Florida Railroad. This connection spurred a real estate boom, bringing in affluent settlers and visitors. By 1885, the Florida Congregational Association chose Winter Park as the site of Florida's first four-year college, Rollins College, which began its first term in November of that year. These developments solidified Winter Park as a center of culture and refinement.

The partnership between Chase and Chapman dissolved in 1885, with Chapman selling his stake to Chase for $40,000. Chapman left Winter Park but left a lasting legacy, having built one of its first homes in 1882 along Lake Osceola. Chase continued to develop the community, ensuring it thrived.

One of Winter Park's most iconic landmarks, the Seminole Hotel, opened its doors on New Year's night in 1886. This grand lakeside resort featured gas lighting, steam heating, a formal dining room, and covered porches. Its opulence attracted notable guests, including Presidents Grover Cleveland and Benjamin Harrison, cementing Winter Park’s reputation as a destination for the elite.

Winter Park achieved a significant milestone in October 1887 when it was officially incorporated as a town. This success was due in part to Gus C. Henderson (1862–1917), a self-educated advocate for African American rights. Henderson mobilized the residents of Hannibal Square to support the incorporation, ensuring the African American community's inclusion within Winter Park. This achievement was a landmark moment for what had once been a small frontier settlement. The town continued to grow and evolve. By 1901, Winter Park had electric lighting in key public buildings, and by 1907, a new campus plan had transformed Rollins College. The local community faced challenges, from runaway hogs to the devastation of the Great Freeze of the 1890s, but through resilience and ingenuity, Winter Park thrived.

Today, Winter Park stands as a testament to the vision of its founders and the rich history of its community. Inspired by this legacy, establishments like The Chapman celebrate the elegance, warmth, and history that define this unique city. Visitors are invited to step into a story where past and present converge, experiencing the art of fine living that began with a dream over a century ago.