Caroline is a rural town southeast of Ithaca bordering Cortland and Tioga counties. Aside from the hamlet of Brooktondale, there are no densely settled areas. There is some farming, but much of the town is forested, including state forest land. Caroline borders Danby to the west, Dryden to the north, the Tioga County towns of Richmond and Berkshire to the east, and Candor to the south. Residents send their children to Caroline Elementary School, a part of Ithaca City Schools, and then to Ithaca for middle and high school.
Western New York was sold off in large tracts after the Iroquois Confederacy was dispossessed of the land after the Revolutionary War. Most of what is now the town of Caroline was originally part of the Watkins and Flint Purchase of 1794. Originally part of the town of Spencer in Tioga County, in 1811 Caroline added some parcels from the adjacent town of Dryden (which was part of the Military Tract) to the north and joined Tompkins County. Six Mile Creek was formerly dammed in many places and mills of all kinds were built. At one time, the creek supported 23 mills, including grist, fulling, and woolen, flour, and saw mills. By 1929 the town was thriving with four railroad shipping stations and sixteen elementary schools. Deindustrialization and the decline of farming through the 20th century has made Caroline a bedroom community of Ithaca. Under the aegis of Town Supervisor Don Barber, in 2004 Caroline became the eighth municipality in the state to purchase wind power to provide part of the municipal electrical needs. In 2005 it became the second municipality to purchase wind power for 100 percent of its electricity use.