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Dutch traders came up the Hudson River in the mid-1600s to explore the area now known as central New York, including the region that would become the town of Springfield in 1797. In 1778, during the Revolutionary War, Springfield and the surrounding settlements were burned by Joseph Brant. As a result, George Washington ordered the Clinton-Sullivan Campaign to break the power of the Iroquois Six Nations. When the Great Western Turnpike (now US Route 20) was extended westward in 1808, Springfield, a farming community, developed more businesses to accommodate a growing population. By the mid-1800s, hops had become a major industry, and many Springfield farmers grew them until a blight destroyed the crops in 1913. After 1920, dairy farming increased as a result of improved technology in cooling and shipping. Today, Springfield offers many attractions, including Glimmerglass State Park on Otsego Lake, Glimmerglass Music Festival, and the second-oldest Fourth of July parade in the nation.

The village of Washingtonville and town of Blooming Grove contain a rich history that extends from early settlement by the Lenape people of the Delaware Nation to colonial European settlement in the 18th century and expanded regional development through the 19th and 20th centuries. Blooming Grove is naturally defined by Schunnemunk Mountain (Lenape for "excellent fireplace") and the Moodna Creek, which is referred to as "Waoraneck" by the Lenape and "Murderer's Creek" in early written documents. The fertile soil along the creek's banks attracted farming and milling industries to the region. Despite the loss of historic structures due to floods, fires, and other disasters, many of Washingtonville's iconic landmarks still remain. Some visible reminders of Blooming Grove's past include the Moffat Library of Washingtonville, a national and state historic landmark; Brotherhood Winery, established in 1839 and considered the oldest winery in the United States; and the Moodna Viaduct, which has been in continuous use since its completion in 1908.