In 1779, the first division of the town into five school districts was made. Eventually the town was to have 18 such neighborhood districts, plus some shared with neighboring towns. Between 1833 and 1893, each of these schools was governed by its own prudential committee or school board.

All children in one district, ages 5-17, attended school together in one room with one teacher. Each level, called a grade by 1890, would work with the teacher at separate times, practicing assigned lessons on their own while other levels were learning aloud or at the blackboard.

As the population center, Woodstock Village was designated District Number Eight. In 1812, due to crowded conditions in the first school on The Green, village residents raised more than $1,200 to build a brick school next to the courthouse on The Green. This building still stands at the corner of The Green and Mountain Avenue.

Although the school districts had been numbered to eliminate the long, awkward titles initially assigned them, they eventually developed titles based on their geography or the proximity of neighbors. The Town Report for March of 1898 listed the following districts outside the village: West Woodstock, Taftsville, Prosper, Cox, Lincoln, Branch, Pelton, Walker, Curtis, South Woodstock, and Fletcher.