Oakham was first settled by British colonists in 1749 as part of Rutland, and was officially incorporated in 1762. It was originally named Oakhampton, but the name was changed for an unknown reason.
The village of Coldbrook Springs was a part of Oakham, near the Barre line, established on the site of a natural iron spring. A railroad depot was built in nearby in the 1830s and the village eventually included a hotel, tavern, medicinal spa, and a number of houses. The area is part of the Ware River Watershed and now part of the Massachusetts state forest, having been cleared of all structures as a part of the Quabbin Reservoir Aqueduct system.