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:

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