Secluded in the gently rolling hills of northwest Worcester County, the heart of the Commonwealth, the picturesque Town of Oakham has preserved its rural/agricultural and tranquil atmosphere since 1762.  Since no major highways pass through the town nor is there any large commercial development, the town maintains a quaint and unique flavor.  The center, which consists of the town hall, a field stone library, church and small circular common, has not changed since the turn of the century. 

The highest point in Oakham is located at the top of Maple Street, the main street, and rises to a height of approximately 1,200 feet above sea level.   The town is located in the watershed area of the Quabbin Reservoir and approximately 30% of the land is owned by the MDC.  

Oakham's distance from major cities permits the residents to keep their independent and self-sufficient nature.  Small family businesses serve the community's immediate needs and the town depends heavily on its volunteers and part-time employees to ensure the success of its programs and projects.