Brief History of Brown-Proctoria Hotel

Contributed by Pam Brinegar September 1999

Source: the Clark County Republican, 29 December 1916

The splendid hotel building that is the pride of Winchester and one of the most attractive spots in the Blue Grass which stands on the corner of Main and Fairfax streets, is the lineal descendant of hotels that have occupied the same site for one hundred and twelve years; and during those years has maintained a steady reputation for high standards of excellence.

The site of the Rees House was lot No. 67 in the original plot of the town laid out by county Surveyor Thomas Scott in 1801 and was then the property of Peter Flanigan to whom we are indebted for important data in the preparation of this article.

Tersely described the lot was at that time a canebrake in the midst of a forest of stately oaks, the cane growth making the boundary of a depression that extended north and south beyond the town limits.

At this particular point a clearing was made, the depression filled and in 1804 Mr. Flanagan built on the lot a substantial and roomy log house which was the first "tavern" in the town and which became known far and wide as the Flanagan house.

This log house stood on the corner and was a "double-house" of two stories with a hallway between, and had the log kitchen back in the yard separate from the house. In the summer .. the guests ate on a back porch that ran the length of the main building; in the hallway which also served as [the] office thruout the year. It had no fireplace and meal time was a chilly affair. If the weather was too cold the table would be spread in the family room downstairs.

On the fourth of July, 1805 was a notable gathering at the tavern to hear Henry Clay who spoke from the stump of a large burroak tree that stood not far from the present People's Bank. Stumps were then plentiful about where now are paved streets and rough boards were laid from stump to stump which served as seats for the vast throng which gathered to hear the distinguished speaker.

In 1808 Mr. Flanagan sold the property to the Hon. Chilton Allen who in 1818 erected the two-and-a-half-story brick building on the corner which was the nucleus of the building that was before the present one. A year later Mr. Allen sold the property to John Dudley, reserving the site of the Masonic building which he deeded as a gift to the Masons. In 1822 Dudley sold out to Hay Taliaferro who operated the hotel until 1835 when he sold out to Jas. B. Skillman, of Bourbon county. Skillman ran the hotel for some time but with poor success and failing to meet deferred payments the property was sold by decree of court the purchaser being Peter Flanigan who for the second time became "mine host."

In May 1850 the property was sold to Rufus Lisle who three years later sold to Robert E. Bush and Francis M. Lisle. Bush & Lisle continued the business for about four years and sold out to Dan Scott and William A. Lindsay. The firm built a two story extension on South Main street and carried on the business for about five years when the property passed to Obe Curry and T.C. Hunter. After about a year Mr. Hunter retired and Mr. Curry became sole proprietor continuing as such until about 1867 when Maj. W.E. (sic) purchased and took possession of the property.