Restaurant guide: Winchester’s dining renaissance from BBQ to cupcakes to moonshine

Just a few years ago all the culinary action – if you can use that term – in Winchester was at the bypass where the predictable national chains fired up their deep fat fryers for drive-thru customers.

But that all began to change about five years ago when several entrepreneurs began opening restaurants, coffee shops, a specialty bakery, a craft brewery and even a distillery within view of the county courthouse’s gilded spire. It would take several day trips for visitors to sample all the local offerings and drive home legally.

You can now drop in to Cairn Coffee for a specialty brew in the morning, stick around for a slab of ribs or a pulled pork sandwich at In and Out Barbecue for lunch, stop in at Wildcat Willy’s Distillery or Abettor Brewing for a cocktail and appetizers and then sit down for a more intimate dinner at Loma’s or La Trattoria.

Kenny Allen, owner of In and Out Barbecue at 1 North Main thinks he and the others who are part of this renaissance hit on a trend that existed before the COVID pandemic and has been strengthened by it. “People want something real,” he said sitting at one of his booths as meat cooked in a huge smoker out on the sidewalk (you don’t have to search addresses to find In and Out, just follow your nose) and customers stopped by to say “’bye, love you” after their lunches.

And the town, Allen said, has been so supportive that his business increased with the lockdown as businesses ordered in food for their workers. “In a small town like this we need to stay unified, help one another.”

Here’s a rundown, in no particular order, of a few of the locally-owned eating and drinking places to visit in Winchester:

Abettor Brewing

301 W Lexington Ave.; abettorbeer.com; (859) 385-4848

Opened only about a year ago after Tyler Montgomery spent the best part of four years looking for the perfect spot and then renovating the one he found. Customers can now enjoy Abettor’s flagship “Pale8” named after and brewed with the hometown soft drink Ale-8-One that is a Kentucky legend.

Cairn Coffee

17 S Main St.; cairncoffee.com; (859) 737-2000

Located across from the courthouse, Cairn Coffee was founded by Calvary Christian Church as a mission in 2012 and purchased in 2018 by current owner/operator John Dixon who still partners with the church. It boasts the “freshest coffee in town, roasted in-house by our roastery, Rocco’s Coffee Roastery,” along with house made baked goods, sandwiches and salads. A Winchester friend described it as a place with great atmosphere and great lattes, “a perfect place to have a business meeting or take your family out to eat.”

Cupcake Apothecary

49 N Maple St.; facebook.com/CupcakeApothecaryLLC; (859) 556-9833

Sara Pifer opened Cupcake Apothecary last summer in a building at the corner of Main and Cleveland Avenue that formerly housed a pharmacy (hence the name) to offer elaborately decorated cakes and cupcakes as well as breakfast items like cinnamon rolls, muffins and scones and, of course, cookies.

The bakery is most proud of their cupcakes - producing more than 180 different flavors since they opened. Every Tuesday they pick five new flavors for the week.

A recent Facebook post described a “decadent” cake with “a layer of edible cookie dough in the center, along with Vanilla Buttercream, Cookie Crumbles and Chocolate Chips!”

Gaunce’s Café and Deli

845 Bypass Rd.; gaunces.com; (859) 744-8664

Gaunce’s Café and Deli is not quite so new to the scene, having evolved from a family market founded in 1954. Through a few moves and changing times the market added deli offerings and then in 2003 the family decided to focus on the deli side of the business. Now in the third generation of Gaunce’s, it remains a family-owned local favorite offering not just deli sandwiches but also soups, salads, baked goods, espresso and smoothies.

In And Out BBQ

1 N Main St.; (859) 314-4385

Kenny Allen began his life in restaurants at 14 washing dishes at a Jerry’s in his hometown of Hazard. Then and there he said he wanted to own his own restaurant one day and now he does, serving up award-winning barbecued ribs, brisket and pulled pork for loyal customers who return time and again as well as newcomers lured by his reputation and the rich barbecue smells that come from the smoker he has on the sidewalk in front of his In and Out BBQ on Main Street.

It’s a small but powerful menu, with some burgers and a few sides, including homestyle fries that one young customer described as “even better than McDonald’s.”

La Trattoria Italian Tavern

30 N Main St.; latrattoriaky.com; (859) 385-4113

Was doing a brisk business when the pandemic hit and the owners pivoted to offering curbside pickup and free delivery with regular Facebook posts about specials and new offerings (notably, an Ale 8 One figures in a photo with one of them — the bacon and blue pretzel burger that includes a half pound of American Kobe beef). La Trattoria is promising a “grand re-opening” soon.

Loma’s at the Opera House

103 S Main St.; lomasatwoh.com; (859) 745-2716

Features traditional favorites like ribeye and shrimp and grits and the occasional breakout special like the vegan grilled Portobello burger stuffed with roasted red pepper hummus. Loma’s, which opened in 2018, is owned by Edward and Vanessa Ziembrowski who bought the 1873 Opera House in 2001 and carried out a renovation that has drawn praise from historic preservationists both in Kentucky and nationally.

Wildcat Willy’s Distillery and Restaurant

31 E Broadway St.; wildcatwillysdistillery.com; (859) 355-5000

Is a special kind of locally sourced restaurant, with many of the ingredients — beef, cornmeal, lettuces, sugar snap peas to name a few — coming from Laura Freeman’s Mount Folly Farm. She and her husband Bill (aka Willy) Kingsbury have also developed the Moonshine Trail to introduce people to more of the craft distilleries sprouting in Kentucky. In 2015 they bought a building that began its life in 1850 as a factory then became a church and parsonage, and an electric company before falling into disrepair. After a complex and complete rehab it started life anew as Wildcat Willy’s distillery and farm-to-table restaurant.

This story was originally published July 8, 2020 at 6:00 AM.