Repurposed Appalachia Series – Brown Proctoria Hotel of Winchester
On the corner of Main Street and Lexington Avenue in Winchester, the Brown Proctoria Hotel still fills an entire city block, its limestone base and brick walls catching the light the way they did more than a century ago. For travelers arriving from the Bluegrass and the eastern hills, this corner was once the first glimpse of modern Winchester. Railroad passengers stepped out within sight of its dome and flagstaff. Motorists on the Dixie Highway and the Midland Trail steered toward its name on postcards and matchbooks that promised “wonderful meals” and restful furnishings. The Brown Proctoria was built to be the city’s front parlor, and for much of the twentieth century it lived up to that ambition.
This is the story of how one downtown lot evolved from an early frontier inn to a four story hotel that tried to claim Winchester’s place as a gateway to the Kentucky mountains, and how that building has survived through decline, abandonment, and renewed preservation.
From tavern lot to Rees House
The story begins long before the Brown Proctoria’s cornerstone was laid. When Winchester was laid out as the seat of newly formed Clark County in the 1790s, the corner that would later hold the hotel was Lot 67 on the original town plat. Around 1804 Peter Flanagan built a log tavern on the lot along the Lexington and Mount Sterling road, taking advantage of traffic that moved between the older Bluegrass towns and the settlements toward the foothills. Within a year he sold the property to Chilton Allan, who replaced the log structure with a brick inn that grew into one of the best known hostelries in central Kentucky. According to later county histories and the Brown Proctoria National Register of Historic Places nomination, guests like Andrew Jackson and other notable travelers stopped there on journeys between Nashville, Washington, and points west, tying the lot to the long arc of national travel history.
During the nineteenth century the inn passed through several hands, eventually becoming known as the Rees House or National Hotel under Major W. E. Rees. By then Winchester was a small but significant town on turnpikes linking the Bluegrass and the mountains, and the Rees House served both local residents and commercial travelers. Descriptions of downtown in late nineteenth century guidebooks like W. M. Beckner’s Hand Book of Clark County and the City of Winchester, Kentucky emphasize court days, rail connections, and hotel corners, showing how important a prominent inn was to the public life of the square…