Orlando History

Discover the stories that shaped our city

From pioneering settlers and visionary civic leaders to iconic landmarks and hidden historical gems, Orlando's past is rich with fascinating tales. These are the people who built our community, the buildings that defined our skyline, the bridges that connected us, the lakes that shaped our landscape, and the moments that transformed a small town into the vibrant city we know today. Through historical accounts and archival discoveries, we preserve and share the stories behind the places and faces that made Orlando extraordinary.

Merrywood Is the Gamble Rogers Mansion All of Winter Park Is Talking About

Merrywood, the largest home Gamble Rogers ever designed, sold for $15 million and faces the wrecking ball. Here’s the story behind the house.

The Colonial Drive-In Gave East Orlando 37 Years Under the Stars

Remember the Colonial Drive-In? From a free Ford on opening night to its final show in 1992, here's the story of east Orlando's 550-car movie lot.

The American Building Was Downtown Orlando’s Great Shape-Shifter

The American Building was a Dodge garage, an office hub, and an insurance HQ on South Orange Avenue. Here's the story of Orlando's lost shape-shifter.

Frisch’s Big Boy Once Ruled West Colonial Drive, and Orlando Still Remembers the Tartar Sauce

Frisch’s Big Boy fed west Orlando from 1968 to 1992. Relive the West Colonial burger spot, its striped-pants mascot, and that famous tartar sauce.

Lil 500 Gave Fern Park Nearly 54 Years of Go-Kart Glory

Lil 500 Go-Karts thrilled Fern Park for nearly 54 years. Meet the Kline family, the scorching steel slide, the Fun Spot link, and why it closed.

Sanlando Springs Was Where Greater Orlando Went to Cool Off for Decades

Sanlando Springs had high dives, slot machines, and wartime dances. Here's how Longwood's favorite swimming spot ended up behind a guarded gate.

Ohev Shalom Grew From a Single Downtown Room Into Orlando’s Oldest Synagogue on a Maitland Lakefront

Ohev Shalom is Orlando’s oldest synagogue. Trace its story from a 1917 one-room building downtown to the lakeside Maitland campus it calls home now.

Dolly Parton in Orlando: The Show We Lost and the Legacy That Stayed

Dolly Parton died Aug. 25th at 80. Inside her real Orlando history: the Vineland Ave. dinner show, Flight 925 and books still arriving locally.

The Metcalf Building Has Outlived a Bank, a Boom, and a Dive Bar

The Metcalf Building has anchored downtown Orlando since 1923: bank tower, Disney's secret office, dive bar landmark. Inside its next chapter.

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A newsletter born from a simple belief: Greater Orlando deserves better local coverage.

Orlando History

Discover the stories that shaped our city

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