The letters mostly concern Winter's work, family and various society events. Addressed from various locations in New York; Washington; and Kerhonkson, New York.

The letters mostly concern theatre-related business; several mention Edwin Booth. Several letters on letterhead of Ford's Opera Houses and Theatres, Baltimore, and Edwin Booth's Southern Engagements. One item on letterhead of the Queen City Hotel, Cumberland, Maryland.

Many refer to Winter's various writings. Most on letterhead of The Evening post, New York.

The letters concern Winter's professional relationship with Harrington as a dramatic writer. On letterhead of the New York Dispatch, No. 11 Frankfort St., New York.