Shepard Settlement is a farming hamlet in the northeastern part of the Town of Skaneateles in Onondaga County, New York. Named for the first settlers, this was the second community founded in the Town of Skaneatles, after the Village of Skaneatles at the northern end of Skaneateles Lake. Other early settler families with numerous members in the immediate include the Chapmans, Bishops, Horsingtons and Hares. The settlement was along Stump Road between Hoyt and Foster Roads on the west and Shepard Road on the east, centered roughly where Chapman Road ends at Stump Road. The hamlet was 2.6 miles WNW of the Village of Marcellus and 4 miles NE of Skaneateles. The various amenities of a rural community, such as a church and general store, have long since disappeared, leaving only Shepard Settlement Cemetery on the northwestern corner of Stump and Foster Roads to establish the community's identity.