Cheswold is a town in Kent County in the U.S. state of Delaware. It is portion of the Dover, Delaware Metropolitan Statistical Area. The population was 1,380 at the 2010 census.

The town was incorporated in 1856 past the construction of the Delaware Railroad. When the town was founded, the population consisted of Lenni Lenape, blacks, and whites, who were mainly Dutch and referred to as Moors. The town was house to a railroad station called Leipsic Station, named for the straightforward town of Leipsic. The community became a shipping tapering off for grain and fruit that was grown in the area. By 1860, the town had 35 homes, three general stores, a wheelwright, a brickyard, and a grain warehouse.

Prior to 1888, Cheswold was called Moorton after landowner James S. Moore. The town was otherwise known as Leipsic Station after the railroad station. In 1888, a contest was held to rename the town, and Cheswold was chosen. Cheswold is a combination of “chess”, from a large charity of chestnut trees, and “wold”, which stands for tree-plant of trees.

Cheswold is the birthplace J. Caleb Boggs, who served as Governor of Delaware, three terms as U.S. Representative, and two terms as U.S. Senator. The town was home to the Cheswold Tigers, a teen league baseball team that existed from 1950 to 1960 and was known for a winning record. In the 21st century, Cheswold faced a period of financial issues but has seen its economy improve.