A story of growth, decline, and renewal on Old Tampa Bay

Oldsmar’s history, and its very name, are both traced to automobile innovator and manufacturer Ransom Eli Olds. By the early 1900s, Olds was one of the leading automobile manufacturers in the country. He sold his first car company, Oldsmobile, and immediately founded his second, the R. E. Olds Car Company, later shortened to Reo, to avoid a potential lawsuit with Oldsmobile.

Reportedly growing restless with the auto industry, in 1916, Olds purchased 37,541 acres of land at the north end of Tampa Bay from a Michigan-based trust company. The property straddled the Hillsborough-Pinellas county boundary, with about two-thirds of the acquisition in Pinellas and about one-third in Hillsborough.

A hotel, called the Wayside Inn, opened on March 31, 1917, with Olds and his wife as the first guests.

It was soon joined by a post office, a general store, and a bank building. State Street was the main business street, and the entire town was platted like spokes of a wheel, with the central hub located on the shores of Tampa Bay. While the plan resembled that of Washington, D.C., the symbolism of the wheel and its connection to the automobile is undeniable.