By 1814 thirteen school districts has been established in town (Haddam Neck had its own school district and two partial school districts [Pine Brook and Middle Haddam] it shared with Chatham (East Hampton). Each district erected a schoolhouse (most were "one room") to serve area students. District schoolhouses remained in use until the early 20th century.

There are a number of remaining historic schoolhouses in town which are now privately owned and have been converted for commercial or residential use. These include the Turkey Hill School, Tylerville School, Shailerville School, Ponsett District School and Burr District. A few of these historic buildings have been incorporated into larger buildings such as the parish hall used by St. James Episcopal Church on Killingworth Road. The Shailerville Schoolhouse has recently been restored and appears much like it would have in the 19th century.

The "Old Green School" building, a later mid-19th century school building, still stands in the center of Higganum across the street from the Higganum Green on Candlewood Hill Road. This Greek Revival style building probably dates from the 1840s when Higganum was experiencing a population boom with the community's growing industy. This building which was originally located across the street on the green was used until 1894 when the Higganum Union School (pictured above) was erected. The "Green School" was later moved (1898) to its existing location by Clark Cutaway Harrow which used it as a store. It is now privately owned. Higganum Union School stood on the Green between 1894 and 1951 and was replaced by Haddam Elementary School located on the opposite side of Saybrook Road. Trivia: Toilets arrived at the Higganum School in 1929.

First District Schoolhouse: Built in 1866, the schoolhouse is one of six remaining district schoolhouses remaining in Haddam. In 1814 the town established 14 school districts and the first school district extended from Higganum's border south to Shailerville. The district schools were used into the 20th century and in the early 1950s a new elementary school was built in Higganum which is still used today.

Early Education: Prior to establishing separate districts, a schoolhouse was located in the village and the schoolmaster would teach there for three months out of the year and then travel throughout the rest of the town for the remainder of the year. Traditionally children attended school for 10 -12 weeks in the winter and 10-12 weeks in the summer, when they were not needed to work on the farm or at home. Men generally taught in the winter months and women in the summer months

Brainerd Academy: Located behind the First Congregational Church of Haddam and accessible by Field Park Drive, this imposing granite-faced building was built in 1839. Originally three stories tall, the building once featured a central bell tower. John and Nehemiah Brainerd organized Brainerd Academy "with an interest to devote forever to the accommodation of Schools of Learning and purpose of education." The school which admitted girls as well as boys was a college preparatory school offering Greek and Latin. The school served primarily New England students, although several came from the south and abroad including Ceylon. The Academy remained open into the 1890's and when it closed, was purchased by the Hazen Foundation. After the town hall burned in 1929 (see courthouse green) this building was used as the town hall and the third story was removed and the two-story portico was added to the façade.

Haddam Neck School House: Haddam Neck was the fourteenth school district in Haddam and this school house was the third and last school building to be erected in the Neck. Built in 1822 the building was originally located across the street on the southeast corner of Quarry Hill and School House Hill roads. In 1916 it was moved to its present location next to the Congregational Church and continued to be used as a one-room school house until 1925. The building is used today by the church as its parish house.