Recorded in the Shelby County Illinois Courthouse, Deed Book 17, page 557, is the plat laid off by Simon Huggins and P.C. Ryder for the town of Windsor. Huggins and Ryder had purchased sections of land along the line that the Terre Haute and Alton railway would be built, with the intent to establish on these properties.
The section on which Windsor would be established was purchased as 320 acres each by Huggins and Ryder, dated November 30th, 1855. The first deed from Huggins and Ryder to buyers would be to Keller and Cunningham, June 17th, 1856. John Cunningham in later years, a resident of Mattoon, Illinois, would tell of his partnership with Keller in the first business place in Windsor, situated on the NE corner of Maine and Pine. Lee H. Keller purchased two lots north of this on June 18th, 1856.
Dr. Jesse W. York is listed as the next purchaser of two lots in block 13 on November 12th, 1856, and J.D. Bruce purchased lot 12 in block 21 on November 20th, 1856. It was on this lot that he built a hotel on the NW corner of Maine and Pine. Early accounts state that he, anticipating the railroad construction, built the hotel in March, moving his family into it before it was completely finished and immediately began to take in roomers.
It would be in this hotel, that a few years later Abraham Lincoln would be a guest. While Mrs. Bruce was preparing his breakfast, Mr. Lincoln held the Bruce's small daughter, Belle, on his lap. He gave Belle a coin which she kept for many years.
Now-concerning the name "Windsor". Various times in Windsor's history, individuals would inquire why the name was chosen and by whom. No one ever found the answer. So the chosen name of Windsor remains a mystery. Supposedly, Illiopolis was the name chosen for it but it changed when it was discovered another community had existed with that name. But the name "Windsor" was so chosen and declared by May 16th, 1856, when the legality of its establishment was registered at the courthouse.