In 1900, Florida was the 32nd largest state in the country with a population of 528,542. At the time, Florida was the South’s smallest state by population. However, the seeds for rapid growth in the 20th century had been planted during Reconstruction and Gilded Era railroad and hotel investments. Here are the state’s five largest cities ranked by population in 1900, starting with the state’s largest city at the time: Jacksonville.

1. Jacksonville

1900 Population: 28,045

Jacksonville was founded by Isaiah D. Hart in 1822. Hart and adjacent landowners began laying out their plans for the town after Spain ceded the Florida Territory to the U.S. in 1821. Jacksonville was incorporated as a city in 1832. By 1860, Jacksonville had grown to become Florida’s third-largest city, behind Pensacola and Key West, with 2,118 residents. Occupied by the Union four times during the Civil War, the city became a desired destination for formerly enslaved people from surrounding plantations. Significant growth led the city to become Florida’s largest by 1870. Key West would overtake the city and remain Florida’s largest for the next 20 years. However, the 1880s transformed Jacksonville into a major railroad hub and port. By 1895, Jacksonville had become the state’s largest city for the second time. It would hold this title until 1950 and regain the title for good after its consolidation with Duval County in 1968.

2. Pensacola 

1900 Population: 17,747

First settled by the Spanish in 1559, Pensacola’s original founding predates the establishment of St. Augustine by six years. However, due to a hurricane, the city was abandoned and not re-established until 1698. Nicknamed “The City of Five Flags,” the city was officially incorporated as a municipality in 1822. Between 1850 and the Civil War, Pensacola was Florida’s largest city. Experiencing rapid post Civil War growth, Jacksonville surpassed Pensacola as Florida’s largest city by the 1870 US. Census.

3. Key West

1900 Population: 17,114

Permanently settled on January 19, 1822, Key West is the southernmost city in the contiguous U.S. Approximately 95 miles north of Cuba, Key West had become the richest city per capita in the country by the 1830s. Prior to the Civil War, the city grew to become a major center of salt production, wrecking, turtling and fishing. While Florida seceded from the U.S. during the Civil War, Key West remained in Union control due to the presence of its naval base. Like Jacksonville, Key West rapidly grew during Reconstruction. Between the late 1870s and early 1890s, Key West was Florida’s largest city. In 1890, it became the first city in Florida to surpass 10,000 residents. However, limited to 5.2 square miles with no room to grow, the city was surpassed for good by Jacksonville in 1895.

4. Tampa

Population: 15,839 

First settled in 1823, Tampa was incorporated as a village in 1849. Originally called Tampa Town, its name was shortened to Tampa in 1855. By the 1850 census, Tampa’s population had increased to 974 residents. Cities such as Apalachicola, Fernandina, Monticello and Tallahassee were all larger than Tampa between 1860 and 1880.

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During the 1880s, Tampa turned into a boomtown due to the discovery of phosphate in the region, the arrival of Henry B. Plant’s railroad and Vicente Martinez Ybor’s moving his cigar operations to Tampa and establishing Ybor City. By 1890, Tampa had grown to 5,532 and become Florida’s fourth-largest city. 

4. St. Augustine

Population: 4,272 

Founded in 1565, St. Augustine is the oldest continuously inhabited European-established settlement in the contiguous U.S. St. Augustine was Florida’s largest city, with a population of 1,708, when the first U.S. Census for the Territory of Florida was taken in 1830. After 285 years holding the designation, St. Augustine was surpassed as Florida’s most populous city by Pensacola in 1850.