Some time ago, I wrote about the pre-Civil War houses in Winchester. This article focuses on the downtown commercial buildings erected before the war and still standing today.
Dodge’s Store Rooms/McGuire’s Pharmacy
Corner of Cleveland and South Main
Often referred to as the oldest commercial building in downtown, it was constructed by David Dodge on a lot he purchased in 1811. According to our early historian, James Flanagan, Dodge built his store house in 1813–1814. The building was described in a survey of historic sites in Clark County. “Beneath a late 19th century face-lifting are hidden the walls of the earliest commercial building in downtown Winchester. The only evidence of this fact is visible in the walls themselves, which are laid in Flemish bond.”
An 1821 ad in the Kentucky Gazette stated, “For Sale, a very valuable two story Brick House and Lot. This house stands at the corner of Main and Short-streets [now Cleveland] and the Lot extends on Main-street to Main-Cross street. The house was built by David Dodge and conveyed by him to Robert Clarke [1818] and by Clarke...to the Winchester Commercial Bank [1819]. The lower part of the building is occupied at this time by Charles C. Moore & Co. as a Store.”
Charles Moore and his brother Thomas R. Moore ran a clothing store on the first floor until the 1830s. Thomas rode horseback to Philadelphia to purchase goods, which were hauled by wagon to the Ohio River and by flatboat down the river to Kentucky. The building later housed the Clark County National Bank (1877), a butcher shop, barbershop, and dry goods store. In 1901, the store rooms were occupied by Mrs. F. H. Haggard. She had a millinery shop on the first floor. She and her husband, city attorney Frank H. Haggard, resided in the upstairs living quarters. The building housed McGuire’s Pharmacy for more than fifty years.
Masonic Lodge
12 West Lexington Avenue
In 1840, Chilton Allan donated a “House and Lot” on Fairfax (now Lexington Avenue) to the “Winchester Lodge of Ancient York Masons number twenty.” Lodge No. 20 had been established by the Grand Lodge of Kentucky in 1812, and Allan was a charter member. One source states that the Masons tore down Allan’s old house and put up a new two-story, five-bay building on the site, which adjoined Peter Flanagan’s hotel lot at the corner of Main and Lexington Avenue (now the Brown Proctor). In 1887 the Masons added a third floor and extended the building one bay to the west.
The Masons used their lodge until moving into new quarters in 1907. They sold the building to N. Rol Ratliff, who in turn sold to Hiram P. Burch in 1914. The following year, Dr. Russell Henry leased the upper floors to open a private hospital, the Henry Infirmary. The infirmary operated for two years, closing when the Clark County Hospital opened. W. R. Sphar acquired the building, which he rented for apartments on the upper floors and businesses on the first floor. The latter included at various times a bus station, grocery, novelty shop, insurance office, taxi stand, jewelry store, and others. In later years, the building suffered a fire and has been unoccupied for decades. At present, it is in very poor condition.
Clark County Courthouse
Main Street
The historic Courthouse was erected in 1855 by the noted architect and builder John McMurtry. The county jail stood behind the courthouse and was surrounded by an 18-foot-tall stone wall that gave the name to adjacent Wall Alley.
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In 1938, the county had the Courthouse remodeled with a large addition on the west side that turned the T‑plan into an H‑plan. The design and materials match the old section and, with the brick painted white, the addition is not readily apparent. Over the years ‚the courthouse was home to a number of local agencies, including the health department, coöperative extension office, emergency services, and a library.
The original tower was replaced in 1889 with one designed by the local architect E. N. Lamm. In 2017, the old tower was taken down, and the following year a new tower was raised—topped by a gilded dome. The courthouse is listed on the National Register of Historic Places.
Presbyterian Church
109 South Main Street
The First Presbyterian Church of Winchester has been at several locations. In 1857, the congregation moved to a new building that they erected at 109 South Main. The Presbyterians remained there until 1893, when they moved again. The old church housed a fruit market and a skating rink for a time before the Sun-Sentinel moved in and stayed for a decade. The Main Street Church of Christ purchased the building in 1918. It was their home until 1957, when the congregation sold the church to the Winchester Public Library. The library remained there until a new building was erected on Burns Avenue in 1998. The present owner is another church, First Baptist Church.

