School District No. 2 was established after 1812 and it managed the finances of and performed adminstrative tasks for schools in the towns of Caroline and Dryden in Tioga County and Richford in Tompkins County during the late 19th century and early 20th century.

In the early 1800s, many families were immigrating to and settling in Tompkins County increasing the number of schools, but there weren't enough funds for them to operate effectively until the New York Legislature set up a fund for the support of "common schools" which allowed them to use funds from state land sales for education. In 1812, New York State passed a law that created a system of common school districts and distributed money to each of them from the Common School Fund. School District No. 2 would have been a part of this state educational program. There is no specific date known for its formation, but it would have been after this time and before 1887. Town officials laid out the districts while voters elected trustees to govern and operate the schools. Typical school districts had one- or two-room schoolhouses where children learned reading, writing, spelling, arithmetic, and geography. In order to generate more revenue, schools could charge "rates" or tuition, which prevented many from being able to attend school, but in 1867 a statue passed that allowed for free schooling in New York which meant more kids could afford schooling and the districts grew larger and throughout the years they often changed their borders. The school district officials and trustees managed the taxes, finances, purchase of school supplies, and other administative issues of schools in the towns of Caroline, Dryden, and Richford.