These letters were handwritten while Legg was a student at Wesleyan (1900-1904) and kept by Legg's mother. In 1907, when Legg married, he and his wife, Nellie, typed them up and they were kept in storage until his wife died in 1968. At that point, many of the letters has been eaten by silverfish. In 1972, at the age of 92, Legg went through the half-eaten letters and added some notes and tried to fill in the missing information. The typed transcripts are 175 pages with the letters filling the pages.

The Howard Legg Letters are about life on the Wesleyan University campus while Legg was a student between 1900 and 1904. He wrote about life as a freshman, such as trying to become a member of Delta Kappa Epsilon, as well as his his classes and the work that came with them. He was on the track team and wrote about the practices and meets. Legg was interested in the other athletic achievements of the university, especially when his friends were part of them, particularly the football team. He was a member of various campus groups and described his activities. For the most part, the letters specifically to his father are more business-like than those to the whole family or just his mother. He often mentioned finances in the letters to his father. While it is only mentioned in the very last letter in the collection, Legg delivered a speech, at his commencement ceremony, but the text is not included in this collection of letters.