New café will blend tourism, food, and community

New downtown eatery aims to draw visitors with Southern classics and local flair

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Estimated time to read:

2–3 minutes
cover art
Cover art for the upcom­ing episode of “Finding Kindness,” fea­tur­ing celebri­ty guest host and Kentucky native Crystal Gayle, to be filmed in down­town Winchester in August. 

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. 

Zach Ross and Valerie Smaldone
Zach Ross inter­views Valerie Smaldone about the TV show and the new café. (Pete Koutoulas)

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. 

Monty Hobbs.
Monty Hobbs describes changes to the décor of the build­ing that will house the Winchester Café, com­ing this sum­mer to down­town Winchester. The devel­op­ers plan to pre­serve most of the build­ing’s his­toric fea­tures while adding touch­es of Winchester’s his­to­ry. (Pete Koutoulas)
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