Tucker's Town was founded by the recently-arrived Governor of Bermuda Daniel Tucker in 1616, but the land was found "verie meene", while the harbour itself was unprotected from the weather and isolated from the rest of the island. Tucker ignored these issues and began to lay out a street grid plan � featuring a 12-foot-wide (3.7 m) road�and had a small chapel built, but was unable to attract any migrants from the main settlement at St, George's. The following year, only two or three cottages had been built in the area, and those were inhabited by soldiers manning Castle Island. Once the failure of the Town was acknowledged, the land was allotted to officers stationed at Castle Island, and off-duty soldiers tended to spend their time there instead of at the Island's sentry post. The only civilian presence was the family of the fort commander.
By 1750, a small civilian community�35 families living on 350 acres (1.4 km) of public land�had finally been established, as had a whaling station to support hunting off Bermuda's south shore. In 1758, Governor William Popple regranted the land to a group of wealthy landowners, but this had little effect on the tenants.
In 1780, the Government of Bermuda began an initiative to encourage the cultivation of cotton in Tucker's Town. The move was not commercially successful, as the wrong kind of cotton was grown. By 1834, former slaves owned property in Tucker's Town as part of St. George's large free black population (some 45% of St. George's blacks prior to that year's abolition of slavery).
An 1856 hurricane strike, coupled with frequent waterspouts and tornadoes, destroyed much of the area's pastures and houses. During the American Civil War in the 1860s, hundreds of barrels of gunpowder and saltpetre were stored at Tucker's Town and Smith's Island. In 1862, a 42-year-old black labourer named James Talbot purchased at over 100 acres (0.40 km) of Tucker's Town from the estate of lawyer Benjamin Dickinson
