The earliest mention I could find of February school vacation comes from 1916. A Boston Globe article from December 19 that year noted that the school committee had ordered that "February vacation week [be] cut in half," to make up for lost time due to an infantile paralysis epidemic. The article also says that April vacation week would go on as planned. This suggests that the current tradition of a week off in both February and April predates 1916. This means that the practice predates the first world war, and any suggestion that it began because of wartime oil crises or shortages is likely untrue. 

Throughout the 1930s, there are multiple advertisements in the Boston Globe that targeted parents of students during school vacation week in February. One, headlined "BERMUDA, FLORIDA TOURS FOR SCHOOL VACATION," boasts "personally escorted tours to Bermuda and Miami, Fla, specifically planned for the school vacations in February." Another, with the headline "CRUISES, TOURS FOR SCHOOL VACATION," encourages parents to take advantage of the break by, "indulging [their children's] desire to travel, thereby gaining renewed energy for the school days ahead."

In the 1960s, a series of articles by Dorothy Crandall positions school vacation week as an opportunity for mothers to get creative. In 1962's "School Vacation is Party Time" she notes that " a special luncheon for one's best friends" is a sure bet. How about one centered on the "unusual food of a country studied in school?" or "a skating party with hearty food to follow?" In 1965's "School Vacation Party Ideas," she lays out the perfect menu for a "Pop Art Party," and suggests a "picnic in front of the fire," as another "fab" idea.

A quick survey of a handful of other major cities' school district calendars suggest that Boston is one of only a few where operations shut down for a full week in February. New York is another notable city where it happens, though it's a much more recent addition there. According to a WNYC story from 2012, February vacation week began in the Big Apple during the late-970s oil crisis as "an experiment for the purpose of energy saving." It became a permanent fixture as part of a budget cutting deal between the Board of education and the teachers union in 1991. Connecticut, another state where February vacation week was once a long-standing tradition, has been increasingly moving away from it. According to the Hartford Courant, last year, only 14 of 166 public school districts in the state still had a week off in February. 

It is worth noting that in most – though not all – major city school districts that do not have a week off in February do have two weeks off around Christmas and New Years. That is the case is places like Chicago, Washington DC, and Houston. In New York and Boston, where there is a week off in February, there is only one week (and sometimes on odd extra day or two, depending on when the holidays fall) around Christmas and New Years. Most city school districts have a week off in either March or April.  Almost every state, including Massachusetts, requires by law a minimum of 180 school days. 

In digging around for information, I uncovered two notable articles from early last century that highlight just how long some of the debates we hear today regarding our school system have been around.

Headline from 1901: Limit to Home Work. Somerville School Board Discusses Question
This article notes a Dr. Miles, who had been advocating for the abolition of homework for students below 9th grade. "Within two weeks I have been called to attend a child suffering from hysterical nervousness brought on by overwork in the schools," he noted. The "textbook committee" found his ideas too extreme and worked out a comprimise. They agreed to limit homework to 30 minutes a day for 7th graders, 45 for 8th graders and 60 for 9th graders. With this reduction in homework, they would need to cover more material during the school day. As such, they decided to reallocate classroom time, "radically" reducing the time spent on "non-essential" subjects including "hygiene, drawing and music." 

Headline from 1907: Does the Present System of Public School Vacation Help or Harm the Children?"
"I think there is no doubt whatever that our long summer vacations harm the students," notes Mr. Joseph Lee of the Massachusetts Civic Service League in the opening. He goes on to say that teachers are "unanimous" in their belief that after a summer away from school students return having "forgotten much of what they learned" and "demoralized." He advocates for a mandatory summer school, with teachers and curricula specifically designed for that time of year, with much of the time spent outside doing "nature work, work for the hands, music, painting and reading."  He suggests "numbers and words" will be used to reinforce their winter studies. In closing he notes, "It would save the children, but can we afford it?"