This plain looking cover was postmarked September 5, probably in 1860 based on the notation to the left, in Chicago. It then made its way about 90 miles northwest to Rockford, Illinois (Figure 1).
The cover is franked with a 3-cent stamp that is #26 in the US Scott catalog. That stamp was issued between 1857 and 1861.
The recipient was Anna Peck Sill, who at the time was principal of Rockford Female Seminary. That school still exists today and is called Rockford University (RU). RU's website has this to say about Ms. Sill:
Anna Peck Sill was the first principal of Rockford Female Seminary. She officially opened the school on June 11, 1849, with classes held in the old courthouse building on North First Street, and began hiring staff when the cornerstone was laid by Reverend Aratus Kent on July 15, 1852. She helped the institution flourish and change so that it was conferring baccalaureate degrees by 1882. Principal Sill’s bell, which she rang at the start of each school day, is still used for the opening ceremony for incoming first-year students and at commencement.
In the category of "it's a small world," Rev. Kent is mentioned in another blog of mine, this one concerning an 1833 stampless cover sent from Fort Winnebago, Michigan Territory (now Wisconsin) to Philadelphia. You can read that one here.
Ms. Sill (Figure 3) appears to have been in the educational field her entire life. She was born in 1816 in Burlington, New York and opened a seminary in Warsaw, New York in 1843. From 1846 until she moved to Rockford in 1849, she was in charge of the female department of Cary Collegiate Institute in Oakfield, New York.
She served as the head of Rockford Female Seminary until 1884 when she was named principal emertia. She died at age 73 in 1889 and was buried at Greenwood Cemetery in Rockford. She never married and left no descendants. According to her obituary in the Freeport Weekly Standard of June 21, 1889, 5,000 women had graduated from the school while she was the principal. Jane Addams, the renowned social reformer and Nobel Peace Award recipient in 1931, was among the alumnae, graduating from Rockford Female Seminary in 1881.
I don't have the letter that this cover contained, but based on the notation to the left, Ms. Sill answered the letter sender who I assume was Luther Rossiter. Luther's family must have been among the early settlers in Chicago because while he was born in Connecticut in 1813, his sister Julia was born in Chicago in 1826. His father Newton was in the lumber business, and so was Luther. This business must have been a source of significant wealth because the family eventually settled in Lake Forest, which even in 1867 was described as the "most elegant of our suburbs" by the Chicago Evening Post. The May 4, 1867, issue of that paper listed the names of some of the residents of Lake Forest, "most of whom will be recognized as prominent business and professional men of the city." Luther Rossiter was among that short list.
Luther died at age 75 in 1888. He never married. Despite his prominence as a businessman, I can't find any obituary for him or his place of burial.
Why he wrote Ms. Sill will remain a mystery.
Figure 1 - Front
Figure 2 - Back
Figure 3 - Anna Peck Sill