Most students of Windham history recognize the name of Thomas Chute as the first settler, his name memorialized by the Chute Road and Chute Cemetery, both in South Windham. He and his wife were multi-talented, as he was a tailor, sheriff, landlord, soldier and innkeeper. His wife, tradition says, was the first teacher, trading her skills for, perhaps, provisions provided by the few neighbors in the early New Marblehead settlement.

Schoolhouses, as we know them, did not exist in those early days. Instead, those who taught did so in their own house or sometimes in the Province Fort. Windham was “settled” in 1737 when Chute is said to have landed and Samuel Webb arrived in 1744. It is said that Webb was the first recorded schoolteacher and his class was held in one of the flankers of the fort.

The first schoolhouse was built “a few rods south of the fort, on the opposite side of the road” and at a meeting on Dec. 25, 1772 (no Christmas yet celebrated) the community voted to finish shingling the schoolhouse, which was located opposite the home of John Anderson. An old resident named Cloudman recalled the structure as “rude” and heated by a fireplace. Teachers at this first schoolhouse included Benjamin Moody, John Patterson and perhaps Timothy Kennard.

In 1778, the second schoolhouse was built in the Gambo district (today called Newhall)

In 1790, the old building that housed the first school was given to a widow named Young, who converted it into a house she occupied for quite a few years, and following her death, another early settler, described as “an old Scotch tailor named Angus” lived in the house. It was eventually taken down and replaced by a building called the Anderson School.

Eventually, Windham had 19 individual schools for the elementary grades – up to the eighth grade. School district consolidation began just before 1900 and in 1910 a high school was built, which is now the site of the municipal offices.

The Anderson School, circa 1920, was the second school built in the early settlement of New Marblehead.