Oldsmar

Oldsmar is one of the few American cities founded by an automobile magnate. On April 12, 1916, Ransom E. Olds — the pioneer behind the Oldsmobile and REO brands — purchased about 37,500 acres at the top of Old Tampa Bay for roughly $400,000, intending to build a planned community for working people. His Reolds Farms Company laid out a town first called R.E. Olds-on-the-Bay, complete with churches, schools, a bank, a railroad depot, a sawmill, and dock facilities along miles of bayfront. The venture never matched the vision: by 1923 Olds had sunk over $4.5 million into a town of only a couple hundred residents, and he traded away his holdings at a heavy loss. The community even lost his name for a decade — rebranded Tampa Shores in 1927 before reverting to Oldsmar in 1937.

For the next half-century Oldsmar stayed a quiet bayfront village while the rest of Tampa Bay boomed around it. Its location — wedged at the corner where Pinellas, Hillsborough, and the upper bay meet — eventually became its asset. From the 1980s through the 2000s, suburban growth filled in the city's neighborhoods, commercial corridors developed along Tampa Road and Hillsborough Avenue, and light industry and office parks brought daytime employment. The 2020 Census counted just under 15,000 residents.

Modern Oldsmar leans into its odd, likable mix of identities: founder's-town history at R.E. Olds Park on the bayfront, old-Florida recreation at the Mobbly Bayou Wilderness Preserve, one of the region's largest flea markets, a BMX supercross track that has hosted national-caliber events, and Tampa Bay Downs — the west coast of Florida's only Thoroughbred track — running races just across the county line at the city's eastern doorstep. It is a small city that reads as a crossroads, which is exactly what Ransom Olds bought it to be.