
Downtown Winchester is welcoming a new storefront, eager to serve up community connections alongside a serving of banana pudding. The Winchester Café is aiming to open this summer, bringing along many surprises.
Valerie Smaldone and Monty Hobbs, co-founders and executive producers of Just Do GOOD Entertainment, have selected Winchester as the backdrop for their award-winning television series, Finding Kindness.
The show features celebrity guest hosts, and the first host has already been signed on. It’s a name familiar to Kentuckians: Grammy Award-winning country music icon Crystal Gayle.
“I’m honored to be part of a project that celebrates kindness and community,” said Gayle. “Returning to the state where I was born for something so positive and uplifting makes it even more special.”
With the filming comes the exciting establishment of The Winchester Café.
The café owners are hoping to get the space ready enough for its preliminary inspection by the end of July and to open sometime in August. When the café doors finally open, they will serve breakfast and lunch from 6 to 2 every day.

Planning to serve up Southern classics like banana pudding and ham biscuits, The Winchester Café is hoping to be a tourist destination within our small town. They are also aiming to cater to tourists by incorporating local Kentucky art and history into the décor.
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“We want this to be more than a place to get a hot dog, but also a spot for the community,” said Hobbs.
Hobbs and Smaldone have high expectations for the renovation of the space, which once belonged to Cheesecake and Company and, more recently, to Thee Cake Carpenter. Instead of the former bright pinks, The Winchester Café will be reminiscent of old-school diners, with neutrals balanced out with the glow of neon signage.
A billiards table will take up residence in the café, accompanied by pool memorabilia on the wall behind it. With this addition, along with local art, Smaldone and Hobbs truly want to integrate a sense of community into the space.
But a pool table and local art are not the only surprises Smaldone and Hobbs have set in store. Starting in July, they will welcome celebrities into town. With these celebrities come minor accommodations in the café. If an NBA player shows up to dine at The Winchester Café, there just may be a basketball goal in place of the pool table.
With a heart focused on highlighting Kentucky heritage and catering to Winchester tourism, The Winchester Café hopes to add to the unique charm of the other great eateries in town.


