In early colonial times the present town of Oakham was a virgin forest occupied by bands of Nipmuck Indians who made seasonal camps in the area for hunting, fishing and agriculture purposes.
During the King Philip War (1675-1676) a 150 square mile area known a Naquag became the stronghold for Indian activity. This area included what is now Rutland, Barre, Hubbardston and parts of Princeton and Paxton. Menamesit, just west of Naquag and Mount Wachusett, in present day Princeton, served as gathering places for the Narragansett, Wampanoag and Nipmuck tribes where they planned their offensive against the colonists. At the end of a losing cause, many of the surviving Native Americans left central Massachusetts looking for new homes. Those that remained were forced to live in four "Indian Towns" under close supervision by the colonists. This left the entire area of Naquag open for colonial expansion.
In 1686, five Nashaway Indians, who claimed ownership of Naquag, sold this territory to a group of land speculators from Lancaster for "25 pounds hard cash".
Scotch-Irish immigrants soon began to buy lots in this area and by 1722 the town of Rutland was officially incorporated as a Congregational community.
Beginning in 1742, Scotch-Irish Presbyterians began to buy land in what was then called "Rutland West Wing" (now Oakham) in hopes of incorporating their own town under a Presbyterian form of government.
After two failed attempts to incorporate, due to Rutland's opposition, Oakham was finally incorporated as a district in 1762.
By the beginning of the Revolutionary War, Oakham's population had grown to nearly 600 people. Oakham was strongly pro-revolution and the loyalists in town were forced to leave their property behind and flee to British strongholds in Boston and Canada.
The sixth Massachusetts Turnpike was built between Pelham and Shrewsbury. This 43 mile toll road followed Old Turnpike Road in Oakham and remained in service until 1828; making travel to and from Oakham much easier and faster.
Oakham's 50th Anniversary. Although the Town of Oakham voted not to go to war with Great Britain, when the war finally did break out, Oakham and New Braintree raised a company of 34 Grenadiers, who were sent to Boston to help prevent a British attack.
Oakham's 100th Birthday finds the country embroiled in a bloody Civil War. Although Oakham had a population of less than 1000 citizens, nearly 100 of Oakham's finest men volunteer for service. One fifth of these soldiers would not live to see Oakham again.
The Central Mass Railroad, a branch of the Boston and Maine, opened in 1887, providing quick transportation for both people and goods throughout the East. A Depot in Coldbrook Springs helped this section of Oakham to grow and prosper. Coldbrook Springs at its peak had two hotels, a post office, a bowling alley, a store, a basket company and a large community hall with a market, a sawmill, a school and 35 homes.
Oakham's 150th Anniversary. The population of Oakham (~500 people) is on the decline as people begin to leave the farms and move to the industrial centers.
Oakham enters the depression era with even more bad news. The state had voted to buy all of Coldbrook Springs in order to provide a clean watershed area for the upper Ware River. As part of the Quabbin Reservoir construction project water from the Ware River would be sent via an underground aqueduct to provide fresh drinking water for the Boston Metropolitan area. To create this watershed all the buildings would have to be removed, all the residents relocated and the Railroad Station dismantled.
Oakham's 200th Anniversary. After decades of declining growth or no growth, the population in Oakham rises to 600 people, the same population it had during the Revolutionary War. Oakham's celebration comes at the height of the Cold War and in the midst of the Cuban Missile Crisis.
Oakham's 250th Anniversary. Oakham has lost most of its businesses and farmland and has settled into the 21st century as a quiet bedroom community. The full time resident population has reached nearly 2000 with a higher summer population. Recreation has become Oakham's focal point with two campgrounds and an 18-hole golf course. The abundance of state land in Oakham provides the open space that can be enjoy all year long. Winter recreation includes ice fishing, cross-country skiing and snowmobiles and most of the state lands are open to hunting and fishing. Hiking trails and horse bridle paths crisscross the landscape and the Boston and Maine railroad bed has been converted into a bike trail. The once bustling village of Coldbrook Springs is now a scenic byway with no evidence of its past history except for a lone stone marker put up by the Department of Conservation and Recreation (DCR).