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The 12 daytrips of Christmas in Winchester

On the first daytrip of Christmas

We all went to see. . .

The Pilot View Mini Mart to pull from the case one frosty bottle of Ale-8-One – the soft drink invented in Winchester – and taste its gingery citrusy flavor before hiking to the top of Pilot Knob State Nature Preserve, elevation 730 feet, to catch the view Daniel Boone had all to himself back in the late 1760s.

On the second daytrip of Christmas

We all went to see. . .

Two award-winning, family-owned wineries: Hamon Haven Vineyard & Winery and Harkness Edwards Vineyards, each with charming tasting room and delicious artisan wines to buy by the bottle and taste by the glass. Cheers!

On the third daytrip of Christmas

We all went to see. . .

Three types of birds – quail, chuckers and pheasants – at Quail Point Preserve and Recreational Hunt for a guided hunt. (Non-guided hunts available, too.)

On the fourth daytrip of Christmas

We all went to see. . .

Lower Howard’s Creek Nature and Heritage Preserve and the John Holder Trail, newly reopened for winter walks to see ruins dating back to Kentucky’s frontier era, including those of a two-room log and batten house built around 1856 and that of an early 19th century cabin, the site of a triple murder in 1939.

On the fifth daytrip of Christmas

We all went to see. . .

Five of our favorite words – cupcakes, cake pops, cookies, cakes, cream horns – on the menu at the Cupcake Apothecary, then order a variety of the sweets treats to devour while strolling downtown Winchester’s elevated sidewalk.

On the sixth daytrip of Christmas

We all went to see. . .

Six friends at Abettor Brewing, our team for trivia night at Winchester’s first craft brewery, and to drink great beer and order dinner from the evening’s featured food truck.

On the seventh daytrip of Christmas

We all went to see. . .

Seven cool displays at the Bluegrass Heritage Museum, including a World War I doughboy uniform; the re-created workshop of luthier Homer Ledford and several of his handcrafted dulcimers and other musical instruments; and what could easily be mistaken for Doctor Who’s Tardis but is actually a red phonebooth that helps tell the story of the telephone in Winchester, a tale that begins in 1884. 

On the eighth daytrip of Christmas

We all went to see. . .

Eight flavored coffee blends at Creative Coffee Roastery, including Kentucky Bourbon, Snicker Doodle and Swiss Chocolate Almond – and take home a few freshly roasted bags to savor the flavor of coffee made from Arabica beans grown in the rich soil of Central and South America. 

On the ninth daytrip of Christmas

We all went to see. . .

Nine Main Street shops a hopping with holiday gifts aplenty, from the handcrafted ornaments at Dirty South Pottery to the festive handmade bow ties at Mason on Main to the boutique fashion collections at Sugar Belle’s and So. Much. More.

On the tenth daytrip of Christmas

We all went to see. . .

Ten historical sites on Kentucky’s Civil War Heritage Trail, including Winchester sites on the Clark County Civil War Driving Tour, like the Winchester Cemetery where many veterans, both Union and Confederate, are buried.

On the eleventh daytrip of Christmas

We all went to see. . .

Eleven Beer Cheese Trail restaurants – plus two more for good measure – to sample this Kentucky original that was created right here in Winchester: beer cheese nachos from DJ’s Steakhouse, shrimp and beer cheese grits from Loma’s at the Opera House, beer cheese Philly steak from Wildcat Willy’s, beer cheese hot brown pizza from the Engine House Pub & Pizza Parlor . . . Mmm. 

On the twelfth daytrip of Christmas

We all went to see. . .

Twelve scenes from Winchester’s history depicted in splashy detail on the Kentucky River Mural, including the era of Native Americans, Winchester’s first church and commerce and industry through the centuries.