Covering an area of 21.1 square miles and once known as "Rutland West Wing", Oakham became incorporated in 1762. Secluded in the gently rolling hills of northwest Worcester County, the town has preserved its rural and tranquil atmosphere since. During its growth it was predominantly a farming town, but wagon manufacturing, wire products, hat and bonnet shops provided employment needed by many families.
Oakham center, which consists of the town hall, a field stone library, church and small circular common, has not changed since the 19th century. The town is located in the watershed area of the Quabbin Reservoir and approximately 30% of the land is owned by the Metropolitan District Commission (MDC).