The community of Gilchrist was named for Gibb Gilchrist who relocated and reconstructed the rail line from Port Bolivar to High Island after the 1915 hurricane. After his work as a civil engineer for the Santa Fe Railway, Gilchrist later became the state highway engineer and the first chancellor of what would become Texas A&M University. By 1950, the community had a post office and numerous businesses catering to tourists. As Hurricane Hilda was approaching in 1964, the postmaster installed wheels on the building and hauled it to High Island where it continued distribute mail. Afterwards, the portable post office moved back to Gilchrist.

One significant historical feature of this the community is Rollover Pass. This narrow strip of land got its name from the fact that sailors once used this spot to roll barrels of imported products from the Gulf side over to boats waiting on the East Bay side. By unloading this way, they could import goods to the Mainland and avoid paying fees to the customs agents in Galveston. This also happened in reverse, which allowed exported items to be loaded without formalities. Many years later, during the American Prohibition period, alcoholic beverages were smuggled through this pass. In 1955, Rollover Fish Pass was opened by the Texas Game and Fish Commission with the goal of providing an opportunity for fish to travel to and from spawning and feeding areas of the bay. This caused the pass to become one of the most popular fishing sites in the state.
Painting by Blaze Design