Winchester Rebirth

November 22, 2022

3:23 PM

Photos by Emily Giancarlo

Historic downtown Winchester enjoys a revitalization, with a swath of new small businesses opening in recent months

Just east of Lexington lies Winchester, a small historic city known as the birthplace of beloved Kentucky products such as beer cheese and Ale-8-One. But Winchester has far more to offer than soda and snacks, and in the past few years, a number of longtime residents and transplants alike have stepped up to return the city’s core to its former architectural glory by expanding dining, retail and living opportunities.

Some of the first to see the potential in Winchester were Peggy and Wendy McAllister of Bee & Clover Renovations. The sisters, who live in Lexington, began their first renovation on Winchester’s South Main Street in 2016, purchasing two additional Main Street properties two years later.

“At the time, with the growth of Lexington reaching the outside counties, we felt like Winchester had all this potential that was sort of unrealized,” said Wendy.

The three properties owned by Bee & Clover Renovations – built in 1886, 1890 and 1915 – were attractive to the McAllisters, who wanted to restore the buildings to their original state.

“The houses had been ‘updated’ with drop ceilings and linoleum at some point,” said Peggy, “so there was a lot to strip away. You pull [a building] apart and you either find something great or something horrible.”

“Fortunately, finding something great makes it worth it. And when finding something horrible, it’s better to know what it is and go ahead and fix it,” added Wendy.

Both buildings are now Airbnb/short term rentals, with one housing a restaurant, La Trattoria, on the first floor and the Airbnb above. The sisters are currently beginning renovations on the third building.

Adam Kidd of DAM Holdings LLC is another former central Kentuckian who saw potential in the small city, which has just under 20,000 residents. When looking for a project site near Lexington a few years back, his company homed in on Winchester for many reasons.

“Foremost, we felt that of all the Lexington satellite towns, Winchester – specifically, the downtown – gave us an opportunity to work with a blank slate,” explained Kidd, who moved to Winchester with his wife in 2020. “When we first began work in downtown, most buildings were on their last breath.”

For the company’s first Winchester project, Kidd said the company “picked what we felt was the most unique building in town.”

This unique structure, built in 1906, is known as the McEldowney Building – a six-story office building that happens to be Winchester’s tallest.

“Throughout its life, it has been used for all sorts of things, but we took it back to its original purpose and turned it back into an office,” he said. “After stripping back years of neglect, we put the building back to its original function and gave Winchester professionals the opportunity to start businesses in small office suites – a simple concept but a great necessity for the community.”

He said he considers it “a small-business incubation project,” and providing smaller and affordable office solutions to local professionals has allowed most of the tenants to graduate from their smaller suites to more custom spaces in the building.

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Chad Walker and his wife, Jill, are the owners of downtown Winchester’s Engine House Pub & Pizza Parlor, a casual bar and restaurant where Jill worked in college. Photo by Emily Giancarlo

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Chad and Jill Walker’s Engine House Pizza Pub & Parlor is an example of a business that pays homage to Winchester’s history and past while incorporating modern touches. Photo by Emily Giancarlo

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Chad Walker of Walker Properties, known for the development of east Lexington’s Warehouse Block, became a part of Winchester’s renaissance in a different way. He and his wife, Jill, own and operate the Engine House Pub & Pizza Parlour – a restaurant where Jill waited tables back in college, under original owner Bob Tabor (the business was called Engine House Deli at the time).

“We wanted to do it as a preservation project,” Chad said. The business had gone through several owners between the time Jill had worked there and the time the couple purchased it in January 2020 – just weeks before the onset of the pandemic. While they had hoped to reopen soon after taking ownership, delays pushed the opening to mid-July, when they operated at half capacity for two months before having to temporarily shut down again.

Despite its early challenges, the Engine House is a local favorite, with a regular bar crowd and live music on the weekends. The Walkers, who live in Lexington but who have spent much time in Winchester over the years, have enjoyed watching the downtown’s renaissance taking place in the blocks surrounding their haunt.

“We had looked at property here about 10 years ago; at the time everything was owned by the same four or five owners,” said Chad. “Now, though, there are a lot of new faces – people working together to make Winchester a great place to be.”

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Micki Wright operates Hell’s Half-Acre, a vintage shop and design house featuring unique items from The J. Petermen Company as well as vintage pieces that inpired them. Wright, who formerly lived in Lexington but moved to Winchester in 2007, also owns an Irish pub called Micki’s Irish Bar. Photo by Emily Giancarlo

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Micki Wright also came to Winchester in a unique way.

A longtime employee of the Lexington-based apparel company The J. Peterman Company, Wright said she fell in love with a local house on the Winchester market before she had ever even set foot in the town. She purchased that house, which was built in the 1800s and sits on an acre lot close to downtown, in 2007, and her role in the town has evolved ever since.

After working with her boss, John Peterman, to set up a storage facility for his company, Wright opened Hell’s Half-Acre Vintage Showroom in downtown Winchester. Named after a small Kentucky town where she ended up during a backroads photo shoot for J. Peterman some years ago, the storefront and apparel outlet is brimming with vintage J. Peterman items and other vintage clothing that has inspired the clothing line over the years, offering many one-of-a-kind items and also operating as a design house.

“Over the past 20 years I’ve collected a massive amount of vintage clothing – I’m now at the point where I need to move some things out to make space for new stuff,” explained Wright.

More recently, when Kidd presented her with the opportunity to take over a local bar, she took it. Operating with the tagline “Winchester’s first and only Irish bar” in a space that has served as a bar for more than 100 years, Micki’s Irish Bar celebrated its one-year anniversary this year.

“It’s the kind of bar every town has – everyone knows everyone, best stories, coldest beer,” Wright said. “It’s just that little hole-in-the-wall that makes you feel at home.”

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Owners of The Hall Coffee & Social Club, Jason and Jessie Hall moved to Winchester from Sacramento, California, earlier this year to pursue their dream of opening a coffee shop in a small historic downtown. Photo by Emily Giancarlo

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While it has definitely attracted its share of transplants from Lexington and other nearby areas, Winchester has been pulling in small-business owners from beyond Kentucky as well. Jessie and Jason Hall moved to Winchester from Sacramento, California, earlier this year to open a coffee and social club in the heart of downtown.

The couple, whose collective experience includes electrical project managing and managing a coffee shop, said they had been looking for a small historic town to relocate their young family and start their own business.

“California is not very small-business friendly and it’s always on fire,” said Jason with a laugh. “We started looking around and ended up finding Winchester – we visited it in January and we fell in love, even though it was freezing cold and snowing, which we don’t know how to deal with really.”

In October, they opened the doors to The Hall Coffee & Social Club in a historic building they had purchased months prior.

“Interesting fact: We had already picked the name The Hall, and this building was originally built for a man named Henry Hall,” Jason said. “So it had to be done.”

Like many downtown Winchester business owners, the Halls live above their business, in an apartment they are renovating. They have plans to transform the third floor of the building into an event space fit to host live music.

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Jennifer Wilson moved to Winchester to follow a longtime dream of opening a vintage/antiques store. Her shop, Eve’s Uniques, is named after a business her great-grandmother had in Chicago in the 1950s and features a blend of curated antiques, new items and a line of mineral paints that she says is perfect for refinishing furniture and DIY projects. Photo by Emily Giancarlo

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Down the street is Eve’s Uniques, a highly curated antique store owned by Jennifer Wilson and named after a similar business her great grandmother had in Chicago in the 1950s. Originally from Chicago herself, Wilson had been running a state agency in West Virginia when COVID struck.

“After five months of lockdown, I was entertaining myself one evening looking at real estate,” Wilson explained. “A friend raved about Winchester, so I decided to check it out. I saw this amazing building and had an offer in within two weeks.”

Wilson, who had dreamed of owning a vintage/antiques store for many years, quit her job and moved into the apartment above the Winchester shop. Over the past two years, she has renovated her historic apartment and outdoor space and expanded the original footprint of her shop into two connected storefronts. Carrying a unique mix of vintage, antique and gently used contemporary decor, the store also carries some new gift and decor items, as well as Fusion mineral paint, a product she said is great for giving new life to old furniture.

“I really feel like Winchester is where I am meant to be,” Wilson said. “I have been more involved in this community than any other place I have lived and feel like there is great momentum to continue to bring the Historic Downtown District back to vitality.

“I consider myself very fortunate to have landed here,” she added.

As is often the case in a small town, word-of-mouth and personal relationships are often the best advertising, and community is at the forefront.

“Everything is word of mouth here,” Wright said. “As soon as somebody loves you, everybody pushes people in your direction.”

And support each other they definitely do. Bouncing ideas off one another, frequenting each other’s businesses and supporting the collective efforts to make the town vibrant and fun, this group praises each other openly and brags about other local favorites, such the new local distillery and farm-to-table restaurant Wildcat Willy’s; the local brewery Abettor Brewing; and antique and gift shop Mason on Main.

“We’re not all just developers or entrepreneurs or business owners. We are a group of people that gives as much back to the community as we take from it,” said Kidd.

When asked how local residents like the changes, Kidd said, “People enjoy it.”

“Some of these buildings hadn’t been open for decades – there were parts that had just been boarded up,” he continued. “Every day someone shares a memory or wants to look at these structures that have been closed for so long…[For] every project that gets finished, there’s a part of town that just kind of comes alive.”

Other changes can be seen in Winchester as well. New art galleries are opening, gallery hops and public events are being planned, public murals are being painted, and the new Legacy Grove Park has added 30 acres of public greenspace to the city.

For tourism, Winchester also has selling points.

“From here it takes the same amount of time to get to Keeneland as it does to get to Red River Gorge. You can have very different Kentucky experiences while based in the same city,” said Wendy McAllister. “That’s something you can’t get from the surrounding counties.”

“It’s about ready to burst with excitement,” Walker added. “I can feel it, you know?”