The county seat and the largest city in the county, Rockport was first settled in 1808 by James Lankford and his family. James, his wife and daughter, lived in a cave under the bluff overlooking the Ohio River.
Other families began settling in the area and by 1813, several area neighborhoods were established.
In 1818, the town became the county seat and people moved to the top of the 200 foot high fluffs to avoid the yearly floods.
On the main street of the town were stores, office buildings, the courthouse, jail, harness shop, post office, a large hotel, drug store, shoe shop, grocery feed store and five saloons--each of which kept several gambling tables busy day and night.
The town spread to the north and west with numerous manufacturing facilities, including two flour mills, four tobacco warehouses, three sawmills, two breweries, one carding mill, five wagon and buggy manufacturers, a furniture factory, three brickyards and seven churches.
The town was incorporated in 1844 and, by 1856, boasted 1,000 residents.
With a thriving port, Rockport was known by all who used the Ohio River. However, inland access was improved in 1874 when a rail line was constructed that linked the city with Jasper to the north. Later, in 1906, another interurban rail line linked Rockport to other Southern Indiana cities.
In 1921, the current courthouse was dedicated.
In the 1930's, many sidewalks were laid in Rockport by the Franklin Delano Roosevelt's Depression Era organization, Works Progress Agency (WPA).
The first public housing authority was established in 1961 for low-income housing and retirement-aged residents.
In 1964, a swimming pool was added to the park.