Rebuilding ‘The Face of Clark County’

Work to commence this week on the High Side Project

You may see con­struc­tion sur­vey­ors tak­ing mea­sure­ments on the “high side” of Main Street between Broadway and Lexington Avenue this week. After years—nay, decades—of dis­cus­sions, plans, meet­ings, and fail­ures, Winchester will final­ly see the dream of rebuild­ing that tired old stretch of con­crete side­walks and steps trans­formed into some­thing beau­ti­ful, func­tion­al, mod­ern, and accessible.

The high side project is under­way, at long last!

The Allen Company was the suc­cess­ful bid­der for the project, which is expect­ed to take most of the remain­der of 2025 to com­plete. If every­thing goes accord­ing to plan, the project will be fin­ished by ear­ly November.

Someone asked me why I have writ­ten so much about this project; after all, it’s only one block of Main Street, and most of Clark County’s 37,000 res­i­dents live, work, and shop else­where than this 650-foot sec­tion of Winchester’s down­town busi­ness district.

But pull up your favorite search engine and query “Winchester, Kentucky,” and note how many images appear depict­ing either the cour­t­house or the high side. I’d wager that when most peo­ple famil­iar with our area think of Winchester, the image that pops into their mind is that of this icon­ic block, with its beau­ti­ful Victorian build­ing facades, his­toric lamp­posts, and con­crete steps. 

I think of Main Street as the face of Clark County. Whether you live in or near down­town, in the out­er sub­urbs, or way out in the coun­ty, this is our shared com­mu­ni­ty cen­ter. It belongs to every Clark Countian in that we all have a stake in its appear­ance, its func­tion, and the suc­cess of the busi­ness­es that line its sidewalks.

But that face is weary and worn. It has seen its bet­ter days. It’s a night­mare for peo­ple with mobil­i­ty issues to nav­i­gate. The old con­crete-step jun­gle detracts from the appear­ance of the build­ings. Time for a facelift!

The project

As I men­tioned ear­li­er, sur­vey work was set to begin this week. According to a city newslet­ter, demo­li­tion is sched­uled to start the week of April 14. Construction will begin at the Lexington Ave. inter­sec­tion and work down toward the Broadway junc­tion. Although Main Street will remain open dur­ing each phase of con­struc­tion, park­ing will not be avail­able on the high side of the street in the con­struc­tion zone. City offi­cials are work­ing on alter­nate park­ing arrangements.

Once the high side is com­plete, work will begin on the oppo­site side of the street, which will be much sim­pler as there are no steps. As I under­stand it, it will most­ly replace side­walks, curbs, and land­scap­ing features.

And by the way—those icon­ic lamp­posts will be care­ful­ly removed, stored, and returned to the street once con­struc­tion has ceased.

Businesses in the affect­ed area will remain open and acces­si­ble to shop­pers. However, as we have seen in past infra­struc­ture projects, there is sure to be an impact on busi­ness. I encour­age folks to patron­ize these busi­ness­es more this year; they will need the extra support.

There will be some incon­ve­nience between now and November. But the reward will be a shiny new face of our com­mu­ni­ty. One that is acces­si­ble to all. One that is new and mod­ern but retains the neighborhood’s his­toric nature. One that will offer more side­walk space for din­ing, rest­ing, and vis­it­ing with friends. And yes, there will still be sec­tions with new steps remaining.

I’m hear­ing excit­ing news about busi­ness­es that will be locat­ing in the refur­bished block, includ­ing the now-emp­ty space at the south end of the block where a build­ing had to be razed last year. By next sum­mer (2026), I expect this area to be hum­ming with new ener­gy, much as the oth­er side of South Main has emerged in recent years, with Erika’s Vocal Studio, Mason on Main, Amy’s Asian Kitchen, and Whiskey and Wiles.

By then, when you Google Winchester, you will find images of a beau­ti­ful high side, includ­ing brick walls, dec­o­ra­tive curbs, land­scap­ing, fenc­ing, wide side­walks, and those icon­ic lampposts—and most excit­ing of all, exist­ing and new busi­ness­es fill­ing up all of those storefronts.

You can get all the offi­cial infor­ma­tion, includ­ing more ren­der­ings of the design, and sign up for newslet­ter updates here: Main Street High Side Project — Winchester City Government