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.


