Dickinson is located on a tract of land granted to John Dickinson in 1824, and named after him. A settlement had been established in this area on Dickinson Bayou before 1850. The Galveston, Houston, and Henderson Railroad was built directly through Dickinson. This line was used in the American Civil War to successfully retake Galveston.
The Dickinson Land and Improvement Association was organized in the 1890s by Fred M. Nichols and eight other businessmen. It marketed to potential farmers with claims of the soil's suitability for food crops, and to socialites with the creation of the Dickinson Picnic Grounds and other attractions. By 1911, the Galveston–Houston Electric Railway had three stops in Dickinson, and the Oleander Country Club was a popular destination for prominent Galvestonians.
In 1905, Italian ambassador Baron Mayor des Planches convinced about 150 Italians from crowded eastern cities to move to Dickinson. They joined the dozens relocated there after flooding in Bryan forced them to seek new homes.
Dickinson continued to grow due to its proximity to Texas City, with its shipyards and wartime industries, and later its proximity to the Johnson Space Center.
During the 1920s, Dickinson became a significant tourist destination resulting from investment by the Maceo crime syndicate which ran Galveston during this time. The syndicate created gambling venues in the city such as the Silver Moon casino.
The City of Dickinson constructed a new multimillion-dollar city hall and library complex which was dedicated June 30, 2009. The complex is located at 4403 Highway 3.
In May 2009 the city began hosting a crawfish festival, called the Red, White and Bayou crawfish festival. The city decided in 2018 not to continue with the festival.
In August 2017, Dickinson was devastated by Hurricane Harvey. Ninety percent of the city was flooded during the storm and 50% was destroyed by flooding.