The Historic Eastside was platted by freedpeople in 1869, becoming one of Jacksonville's earliest Black communities.

Built on land east of Hogan's Creek, it grew as a self-determined neighborhood — a place where formerly enslaved families could own land, build homes, establish churches, and create community outside the constraints of downtown Jacksonville.

This act of platting was creative community development in its earliest form: turning land into legacy.

Its main commercial corridor, Florida Avenue — now A. Philip Randolph Boulevard — survived the Great Fire of 1901, which destroyed most of downtown Jacksonville, due to the neighborhood's location east of Hogan's Creek.

During its thriving period, the corridor became an economic haven for Black residents, filled with restaurants, bars, grocery stores, retail shops, and a theater. Known simply as "The Avenue," it was Eastside's version of LaVilla's Ashley Street, connected to downtown by a streetcar line and alive with Black-owned commerce throughout the segregation era.

The Avenue's fortunes turned in the 1960s. In September 1964, Hurricane Dora struck Jacksonville as a Category 2 storm, damaging buildings on Florida Avenue and touching off looting of businesses along the street.

Rising racial tension that decade erupted into rioting that further devastated the corridor's Black-owned businesses. Compounding the damage, the Mathews and Hart Bridges, built in the 1950s, along with a series of expressways and connectors, displaced large numbers of surrounding residents as the city's urban renewal efforts reshaped the area.

The community was never the same — businesses moved away from the once-flourishing corridor, and the Eastside neighborhood entered a sharp decline.

In 2013, a group of residents, small business owners, and stakeholders came together to form the Eastside Community Coalition, acting as a liaison between residents and civic organizations to bring resources to the community as private investment began to return.

In 2016, the ECC became the Historic Eastside Community Development Corporation (HECDC), with a mission to preserve and protect the rich history, heritage, and culture of Eastside. In 2020, HECDC achieved status as a Community Housing Development Organization (CHDO).

This momentum culminated in 2023, when the Eastside Historic District was officially added to the National Register of Historic Places, recognizing more than 675 contributing historic resources and unlocking new preservation and tax-credit resources for the neighborhood.

Building on that recognition, Florida Avenue — the Eastside's historic commercial spine, now A. Philip Randolph Boulevard — earned Florida Main Street designation, making it Jacksonville's first-ever Main Street district and launching a new chapter of corridor revitalization led by residents and business owners.