Jacob Davis, Jr. taught the first school operated by white settlers in Montpelier prior to 1791. Davis was the son of one of the first permanent settlers, Col. Jacob Davis. Davis Jr. taught out of a log schoolhouse on the river near the Middlesex line, according to Daniel Pearce Thompson in his “History of Montpelier from the time it was chartered in 1781 to the year 1860.” Students came from Col. Davis’s household (siblings and boarders), and other families living near him, and from Middlesex and the Dog River area in Berlin. It was the only schoolhouse in the vicinity for about two years, until David Wing, Jr. taught school in the new frame house built by Col. Davis in 1791. Then, according to Thompson, Abel Knapp kept school at a frame schoolhouse built on the road to mills located at Branch Falls. That schoolhouse burned, and a new one was built near the Methodist Church. Classes were then taught by a “college student who somehow found his way into the settlement.” Pupils traveled for many miles to attend this school. In 1794, Montpelier was divided into six school districts to make sure more students could attend school. The Washington County Grammar School was founded in November 1800, and the “Trustees of Montpelier Academy” were organized. From there, a two-story building that contained two large classrooms and an apartment for the teacher and his family was built within the next few years. Money for the building was raised from among citizens of the town. In Thompson’s estimation, “common English education” was taught competently, including reading, spelling, writing, arithmetic, grammar, and geography. The teachers used “modern” textbooks that simplified the sciences for the “ready comprehension” of the student.The best teachers during this time were thought to be Calvin Pease and Jonathan Southmayd; Southmayd, in particular, because of how long he taught in Montpelier (12 years) and his “peculiar combination of fine qualities,” which included social and moral qualities as a teacher and as a man. Most other teachers did not last longer than one or two years.