The history of the Little Red Schoolhouse begins around 1815 when the present building was constructed at the crossroads of Platt Hill Road and Burr Pond Road at Winchester Center to replace the old one that had burned down. Into one end of it a fireplace was built that was to heat the one room building until sometime in the 1830's when a large box stove was installed. The pupils sat a long desks attached to the other three sides until these old wall seats were removed to be replaced by coarse wooden desks arranged one ahead of the other. As the process of new replacing old continued, more up-to-date books were purchased. However, as the years passed, the number of pupils gradually diminished until on August 26, 1908, it was voted to close the District #8 school. Lonely and deserted it stood, only a monument to the past.

During this time, Mr. William H. Hall for whom Hall High School in Hartford is named, wrote an article in the Winsted Evening Citizen stating his concern for the neglected building. A former student, Mr. Clifford Bristol, responded by purchasing the property and restoring it to perpetrate the memory of the Little Red Schoolhouse and for his father, Charles A. Bristol, who had taught there. After completing the restoration he held a reunion for all former teachers and students in June, 1916.

It was not until 1923 that another meeting was held there. This meeting was for the purpose of forming an organizationin the interest of preserving the Little Red Schoolhouse. At this time C.E. Bristol was elected as preseident and in August of the same year it was voted to call the organization "The Little Red Schoolhouse Association" and Mr. Bristol presented the deed to the building to the Association. It was also voted to hold meetings annually as long as interest continued to warrant it.