Shortly after we moved to Winchester in 2015, I read in The Winchester Sun about developments downtown that would ultimately result in a brand new CVS Pharmacy and a Kentucky Bank branch on Maple Street.
The former bank location—at a prominent gateway to the downtown business district—was to be demolished and replaced by the new drug store, while the new bank branch would be built on another corner of Maple a couple of blocks north.
The final result turned out to be a bit of a disappointment, in my view.
I had hoped for a more substantial bank building on this important urban corridor—something more akin to the Central Bank branch up the street or the People’s Bank on North Main, both of which better reflect the urban nature of the downtown business district than the Kentucky Bank branch, which is virtually identical to the suburban-style building built on Bypass Road a couple of years prior.
Similarly, I was hoping the new drug store would at least pay homage to the distinctive building it replaced, with its corner plaza that welcomed visitors downtown. Instead, we got a suburban-style store surrounded by a sprawling parking lot. Not very inviting to pedestrians walking about downtown.
Despite these misgivings, I decided to look at the positive side of these developments. Both of these new buildings represent a substantial investment in our downtown business district by private businesses, an indication their leaders believe there is a future in Winchester’s downtown district.
At a time when most small-town cores are struggling, Winchester’s seems to be picking up steam. One can visit many nearby towns and witness downtowns where no new building has gone up for decades.
Take a look up and down Main Street. I am encouraged by the many dedicated officials, business people, and volunteers who are working to make our downtown more vibrant and interesting. It’s true new businesses tend to come and go, but I sense we are nearing a tipping point.
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I’m especially excited about seeing the high-side project to be completed over the next year or so. The completely renovated building and green space being developed by DAM Holdings at South Main and Lexington Avenue will be an attractive gateway on that end of town. Not to mention the other side of the street, where Whiskey & Wiles’ renovated space, along with Amy’s Asian Kitchen and Mason on Main, make up a great trio of interesting and well-maintained businesses.
I believe the next five years or so will be a boom era for Winchester’s Main Street and environs. It takes time to rebuild a business district that, like most downtowns, was wiped out by the flight to the suburbs in the late 20th Century.
I don’t know about you, but I’m bored with big box stores and chain restaurants. Face it, you could be in any town or city in America along “the strip” and not know where you are. But we have a shining jewel in our mostly intact Victorian-era Main Street. That’s an authentic backdrop you can’t recreate, and is the envy of many small towns.
Just before Christmas, my wife and I did some shopping downtown and enjoyed the pleasant experience of interacting with friendly shop owners and greeting friends and neighbors. We plan to spend more time downtown as warmer weather takes over and we have time to explore all the other great shops and eateries in town. I hope you see you there.
One doesn’t have to own a business or be a town official to help rebuild our downtown; we can all contribute to its success. You don’t have to do anything more than come down and visit. Check out all that downtown has to offer and spend a few dollars where it helps our community the most.

