Winchester could learn lessons in historic preservation from Madison, Indiana

This story was originally published in May 2022. In 2024, the Winchester City Commission passed an “abandoned or blighted urban properties tax” to discourage “demolition by neglect.” However, some observers have complained that the new ordinance is not being effectively enforced. (Editor)
A couple of weeks ago, my wife Clare and I escaped for a two-night getaway for the first time in ages. The destination for our mini vacation was Madison, Indiana, an old river town best known to some for its speedboat regatta held each July, one of the largest hydroplane races in the U.S.
However, Madison is a year-round tourist destination for another reason. The city boasts one of the largest downtown historic districts in the nation. Although smaller than Winchester, Madison counts 133 city blocks comprising an incredible 1,695 properties listed on the National Register of Historic Places. Many of its buildings date from 1810, when the town was established, to the end of its heyday in 1860. Tourism put Madison back on the map in the 20th century.
One other noteworthy feature of the town is the near absence of chain stores and franchise businesses in the historic district. (We found only two, a Citgo gas station and a Dollar General store.) Madison has somehow managed to restrict these types of businesses to an area north of downtown called “The Hill.” Entering Madison from the bridge over the Ohio River, one is immediately struck by its strikingly non-commercial appearance. In contrast, crossing the bridge going south you enter Milton, Kentucky, where the first buildings encountered are gas stations, tobacco shops, a food mart, a car wash, and a place selling lottery tickets. Milton is not a tourist stop.

Winchester cannot rival Madison in the number of historic properties. However, we do have a downtown historic district containing a remarkably intact collection of late 19th-century buildings. The downtown commercial district was listed on the National Register of Historic Places in 1982 with 114 contributing structures. The district extends along Main Street from Washington Street to Ogden Court and includes the Courthouse Square plus a portion of Broadway and Lexington Avenue. The distinctive “high side” of Main Street contains the richest collection of commercial architecture in the district.
Among the things that detract from a vibrant tourist-worthy downtown commercial area are empty storefronts, deteriorating buildings, and gaps in the streetscape.
Empty shop windows send the signal that businesses are failing and the local economy is in a downturn. Just a few years ago there were many of these along Main Street. Winchester is experiencing a kind of renaissance downtown with a host of new property owners. Many buildings have already been restored and put back into productive use. It’s a double win for Winchester that these old buildings have not only been saved but also that they are now contributing positively to the local economy. More projects are in progress.
I’ll risk mentioning only two examples out of the many that could be cited. Laura Freeman and Bill Kingsbury purchased the old A.M.E. Church building at the corner of Broadway and Church Alley from the city. The structure that was near collapse and slated for demolition has been structurally repaired and thoughtfully repurposed as Wildcat Willy’s Distillery and Farm-to-Table Restaurant.

The Odd Fellows Building on South Main Street (the old Winchester Bank) suffered a major fire several years ago and has been sitting empty since. Its loss would have been a serious blow to the downtown landscape. Earlier this year Perry Williams purchased the building and began making repairs to the roof and windows in order to stabilize the structure. Doctor Williams has pledged to put the building back into commercial use. Winchester is fortunate to have many others who are committed to restoring our historic downtown area.
Never miss a thing with our FREE weekly newsletter.
Perhaps the most common excuse for razing a building is that it’s just too expensive, that the cost of restoration could never be recovered. This is typically the case when owners allow buildings to deteriorate by failing to perform proper maintenance (or any maintenance at all). The term for this is “demolition by neglect.” I believe most of us can point to a number of downtown buildings falling into this category. The only way to prevent it is by a local ordinance requiring owners to provide upkeep on their buildings. Winchester badly needs such an ordinance.
There are a number of parking lots (read “gaps”) along Main Street and Broadway where buildings once stood. See the accompanying photos for examples. The loss of historic buildings is rarely due to necessity. Preservationists know that any building still standing has a chance to be saved. Historic buildings provide an important part of Winchester’s identity. They help illuminate our history and culture and together constitute the architectural heritage of our community. It’s one of the things that makes Winchester a nice place to live.
