The district covers 550 acres (220 ha), whose central focus is the Thompson Center Green, laid out when the town was established in 1735.

An early tavern stood on Thompson Hill by 1716, serving travelers on what was then the main road to Providence, Rhode Island.

In 1797, Thompson Hill benefited from the creation of turnpikes which intersected here (now Routes 193 and 200), spurring additional development and traffic.

The town's economic focus passed to its mill villages, effectively ending significant development at Thompson Hill.

It is also the site of the former country estate of Norman B. Ream, which is now home to the Marianapolis Preparatory School; its grounds were designed by the Olmsted Brothers firm.