What’s next for downtown Winchester?

We can create a destination downtown that's the envy of Central Kentucky

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5–8 minutes

The “high side” project to reha­bil­i­tate the blocks of Main Street between Lexington Ave. and Broadway is now essen­tial­ly done, with only minor issues left to address. The World War II/Korean War vet­er­ans’ memo­r­i­al on East Broadway is com­plete and was ded­i­cat­ed on Veterans’ Day.

Our his­toric down­town is look­ing bet­ter, and por­tions of Main Street are now more acces­si­ble, more usable, and more attrac­tive than ever. 

So what’s next?

I believe we are at or very near a tip­ping point in our down­town. We seem to have reached a crit­i­cal mass of unique shops, activ­i­ties, eater­ies, and bars, attract­ing more vis­i­tors to the cen­tral busi­ness district.

The High Side Boutique and The Hall have both reopened recent­ly under new own­er­ship. Thee Cake Carpenter, a new bak­ery, has opened in the for­mer Cheesecake & Company space.

Other recent­ly opened busi­ness­es on Main Street include Birdie’s Attic, Tee’d Off Golf, and Past Time Social Club and Cigar Lounge. 

A new book­store is expect­ed to open in January. The emp­ty build­ing and lot at the south end of the high side block, owned by DAM Holdings, is com­ing along, and I’m hear­ing there’s a good chance a ten­ant will be found by the time the space is ready to be occu­pied. But there are still plen­ty of vacant store­fronts down­town, although occu­pan­cy seems to be as high as it has been in years.

What we do next is cru­cial if we want to keep up the momen­tum and fill more of our vacant store­fronts. Will we con­tin­ue to advance, or will efforts stall, lead­ing to a decline?

More coöperation and promotion

The Winchester-Clark County Chamber of Commerce and the Tourism Commission do a good job of pro­mot­ing our community—not only down­town. But I believe we need a well-fund­ed enti­ty to focus on pro­mot­ing our down­town mer­chants. This could be some­thing the city com­mis­sion funds and orga­nizes, but I believe we would be bet­ter served by an orga­ni­za­tion fund­ed by down­town mer­chants and build­ing owners.

We need more and bet­ter coöper­a­tion in this area, along with more focused adver­tis­ing in the Bluegrass region and beyond, high­light­ing the many unique shops and restau­rants that line our his­toric Main Street. More spe­cial events and sea­son­al shop­ping oppor­tu­ni­ties could draw more shop­pers downtown.

Here’s an idea: why not encour­age down­town busi­ness­es to coop­er­a­tive­ly agree to stay open lat­er on Friday nights in the sum­mer? Many peo­ple do their shop­ping and din­ing in the evenings.

More infrastructure updates

Now that the high-side project is com­plete, we should move for­ward with updat­ing the Main Street streetscape beyond Lexington and Broadway. A new project to update side­walks and street ameni­ties south to Boone Avenue and North to Depot Street would not be as com­pli­cat­ed, time-con­sum­ing, or incon­ve­nient as the recent­ly com­plet­ed project was.

Using the same design pat­terns as the high side on the remain­ing blocks in the busi­ness dis­trict would cre­ate a beau­ti­ful, cohe­sive expe­ri­ence for pedes­tri­ans and dri­vers through­out our main shop­ping district.

It is my under­stand­ing that there is move­ment afoot in city gov­ern­ment to pur­sue state high­way grants in order to facil­i­tate such a project.

Another change that I con­tin­ue to advo­cate for is work­ing with the state high­way depart­ment to allow the city to take over main­te­nance of Main Street. This could involve remov­ing the US 60 des­ig­na­tion, mov­ing it to the four-lane Maple Street.

This would reap numer­ous ben­e­fits. Through traf­fic on Main Street would be reduced, cre­at­ing a slow­er, more inti­mate pace for shop­pers. The city would be free to install fea­tures such as speed tables, cob­ble­stone inter­sec­tions and cross­walks, cus­tom light­ing fix­tures and traf­fic sig­nals, and oth­er ameni­ties cur­rent­ly not per­mit­ted on state-main­tained highways.

All of this would serve to make our Main Street even more beau­ti­ful, func­tion­al, and safer for both pedes­tri­ans and drivers.

Code enforcement

One of the most cru­cial changes I keep hear­ing from prop­er­ty own­ers and shop­keep­ers down­town is the need for stronger, more con­sis­tent enforce­ment of build­ing codes.

Currently, as I under­stand it, the city code enforce­ment divi­sion only inspects new busi­ness­es and responds to com­plaints of code vio­la­tions. I would like to see a more proac­tive process that involves reg­u­lar inspec­tions for exist­ing properties.

I have also heard from some prop­er­ty own­ers that enforce­ment is not always done even­ly. I’ve lis­tened to some prop­er­ty own­ers say they are “harassed” by the city, while oth­ers are free to let their prop­er­ties deteriorate.

Whether true or not, we have seen sev­er­al exam­ples of “demo­li­tion by neglect,” where a build­ing is not main­tained, result­ing in dete­ri­o­ra­tion to the point where it can­not be sal­vaged. The Sphar Building and the build­ing that for­mer­ly occu­pied the emp­ty lot at 71 South Main are recent examples.

A local devel­op­er recent­ly told me that sev­er­al more build­ings on Main Street are in dan­ger of suf­fer­ing the same fate unless repairs and deferred main­te­nance are com­plet­ed soon.

Our great­est asset is our won­der­ful col­lec­tion of old Victorian busi­ness build­ings on Main Street. If we allow many of them to fall into ruin, we’ve made a trag­ic mis­take that can nev­er be corrected.

A livable downtown

Many recent ren­o­va­tion projects have not only improved the street-lev­el retail envi­ron­ment but also added new apart­ments and oth­er res­i­den­tial spaces for peo­ple look­ing to live down­town. This is a very encour­ag­ing trend, because we’re nev­er going to see more gro­cery stores, drug stores, and the like down­town unless enough peo­ple are liv­ing near­by to sup­port them. 

Sadly, the eco­nom­ics of ren­o­vat­ing old­er build­ings dic­tate that most of the new hous­ing units are on the pri­cy side. The result is the same as what we are see­ing in the sub­ur­ban hous­ing mar­ket: extremes of very high-end prop­er­ties on one side, and bare­ly liv­able cheap prop­er­ties on the other.

Like the rest of Winchester, our down­town needs more afford­able hous­ing units to accom­mo­date the peo­ple who most desire to live in urban spaces: young peo­ple who are most­ly priced out of the market.

The future

What can we expect to see in down­town Winchester in the com­ing decade? I don’t know for sure, and nei­ther does any­one else. But I do have a dream.

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Our down­town has had its ups and downs. Like all small towns and many big-city down­towns, we will nev­er return to the days when big depart­ment stores and oth­er large retail out­lets lined our streets. We can com­plain about that, but we can’t change it. What we can do is remake our down­town into some­thing that 21st-cen­tu­ry patrons want: an experience.

I imag­ine a Main Street bustling with activ­i­ty. A diverse mix­ture of “every­day” stores, niche bou­tiques, and shops. A diverse com­mu­ni­ty of shop­pers, some of whom live with­in walk­ing dis­tance, oth­ers from sur­round­ing parts of Clark County and sur­round­ing towns. A safe, walk­a­ble, and bike­able down­town. A place where peo­ple want to be on sun­ny days and warm star­ry nights. A place alive with music, lights, and people.

A down­town like that is some­thing I believe peo­ple are crav­ing. I think we are bored with shop­ping online, with big-box retail­ers and gro­cers, with traf­fic and nav­i­gat­ing acres of asphalt at each store.

If Winchester can cap­ture that mag­ic, our econ­o­my will thrive, more jobs will emerge, and we will be the envy of Central Kentucky.

Main Street from Cleveland Avenue looking south.
Main Street from Cleveland Avenue look­ing south, 11/26/25 (Pete Koutoulas)

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