Most town residents attend Trumansburg Central Schools, but some in the southern part of town attend Ithaca city schools. Ithaca is a 15 to 20 minute drive down Route 96.
Ulysses, named for the hero of The Odyssey, was one of the original townships that made up the Central Military Tract that was put aside for veterans of the Revolutionary War in the late 18th century. The present town is a remnant of the township, which has been carved up to make other towns, including Dryden, Ithaca, and Enfield. Ulysses was settled in 1790 and Trumansburg in 1792. There were mills built along both Taughannock and Trumansburg creeks during the 19th century, but the ones still in use in 1935 were swept away by a hurricane that put downtown Trumansburg under 20 feet of water. Some of the hamlets in town, including Perry City, Waterburg, and Jacksonville, were once small villages, complete with stores and mills, but they are just collections of homes now. In the 20th century Babcock Poultry built up a large operation for chicken breeding at several sites around town, but the firm was purchased by a multi-national corporation in the late 20th century and all operations and the properties were sold.