The town now known as Middlefield was once part of outlying areas of five neighboring towns — Chester, Becket, Washington, Peru, Worthington — plus a large tract of land called Prescott‘s Grant. Twelve families, many from Hebron, CT, found their way to this high and rugged plateau by 1774. They included the households of Samuel and Elnathan Taylor, David Mack, Josiah Leonard, William Mann and Daniel Meeker. Just ten years later, when the town incorporated in 1783, there were 68 resident families.
One of the first orders of business for this new township was to collect taxes to build roads. Only two “good” roads existed; the rest were dozens of ox cart trails. In what locals refer to as mud season (others call it Spring), there was often no way to get from one part of town to another. Over time, thirteen roads were laid out to connect the settlements scattered throughout the town. The next priority was to “site” a meetinghouse for religious worship, community gatherings and public meetings. Its location was a contentious issue for a town cobbled together from five different settlements with no clearly established geographical, political or social center. It took six years and 30 town meetings to reach agreement among the many strong personalities and opposing opinions. On that same meetinghouse site at the intersection of Skyline Trail and Town Hill Road, the Middlefield Church stands today.