Milford's first school was held in teacher Jasper Gunn's home in 1642 before the town's first schoolhouse opened on December 27, 1697. To accomodate the planting season it was only in use for the winter months until about 1718. There were concerns about children running on the yard of the nearby church with the first school playground in Milford in 1857.
The Milford newspaper reported in the summer of 1861 that a group of well behaved boys, "suffered no ill effects from exposure" getting "back to nature" while camping as Indians as "The Buckingham Rangers". Many of the early settlers to the area were very young including Robert Treat who was only at 17 was an already a surveyor when he came to Milford. One story is of 2 teenagers that ran away from their parents home in England to New Haven and eventually settled in Milford.
Milford created 10 school districts on 1797. The last one-room schoolhouse with 1 teacher for 21 student in 5 grades closed in 1926 when many Milford families lived on large farms. Land sales of the closed buildings went towards the school system.
Students testified at the April 1971 Board of Alderman meeting about cuts in the budget for textbooks despite some older than they were. .