McEntee may have executed this scene while summering in Rondout, New York. It reveals that he was working in Durand's tradition.

This is obviously a drawing executed en plein air, whose date is dutifully recorded by the artist in an inscription to underline its authenticity. It preserves a landscape near McEntee's birthplace, where he spent his summers."Rondout," "pronounced "ron doubt," (often mis-pronounced "ROUND OUT") was a village located on the north side of Rondout Creek near its mouth on the Hudson River in Ulster County. The name derives from the fort, or redoubt, that was erected near the mouth of the creek. The Dutch equivalent of the English word redoubt (meaning a fort or stronghold) is reduyt. In the Dutch records of Wildwyck, however, the spelling used to designate this same fort is invariably Ronduyt during the earliest period, with the present form rondout (often capitalized) appearing as early as November 22, 1666. Incorporated on April 4, 1849, Rondout served as a Hudson River port for the city of Kingston located about a mile distant but was later incorporated into it. Its environs served as a popular sketching ground for a number of nineteenth-century artists.

McGoldrick was a distinguished lawyer in New York City and one of the founding partners of the law firm McGoldrick Dannat, etc. He also served as Comptroller of the City of New York from 1938-1945 and wrote, among many books, Law and Practice of Municipal Home Rule, 1916-1930.

Denny was the moderator of an important early radio program entitled "America's Town Meeting of the Air," which was broadcast live from New York City's Town Hall from 1935 to 1956. One of America's first talk shows, it began as a six-week experiment on NBC. The show's introduction tried to evoke the ambiance of America's old town meetings. Denny wrote that it was "…a device which is designed to attract [the average American's] attention and stimulate his [sic] interest in the complex economic, social and political problems which he must have a hand in solving." As Woolf frequently had his subjects do, the drawing is autographed by Denny at the lower center as further testimony to the fact that it was indeed executed from life.