16+ Ideas for Winter Fun in Shelbyville, Kentucky

Don’t let cold temperatures keep you from having fun. Head to the rolling hills of Shelbyville, Kentucky, this winter for fun that spurs long-lasting smiles, whether you prefer invigorating outdoor activities, cozy indoor hotspots, or the best of both.

Horses (of course!)
Kentucky is horse country and Shelbyville is no exception: Known as the “American Saddlebred Capital of the World,” this is where many of the nation’s most famous and accomplished show horses are bred and trained—over 90 stables bustle with activity all year long! Get a behind-the-scenes peek at what’s involved in raising and training Saddlebred horses during a 90-minute horse farm tour. Learn about the breed that has featured in local history since the 1760s when pioneers including explorer Daniel Boone traveled to Kentucky on “American Horses,” the forerunner of the modern Saddlebred. Every farm tour includes a stroll through the barn, a look at the gear and methods used to train Saddlebreds, opportunities to observe the breed’s distinctive gait, and a chance to get close to horses. Undulata Farm, a Shelbyville landmark listed on the National Register of Historic Places, is currently owned and operated by horse breeder and trainer Edward “Hoppy” Bennett. “In winter we’re breaking yearlings,” he says. “We use a calm approach; this is not a rodeo. All these horses are athletes. I’m the coach and it’s my job to decide what role they’ll have in the show ring.” Kismet Farm, located in Simpsonville, also trains show horses plus offers progressive riding lessons for riders all ages and ability levels. If riding sounds like your definition of fun, you can also saddle up at Shelby Trails Park. Bring your own horse or borrow one: guided rides and lessons are available. Explore miles of trails that weave through 462 forested acres on foot or horseback and the adrenaline will help keep you warm even in cold weather.

Kentucky is the world’s top bourbon producer, and Shelbyville is home to one of the state’s newest distilleries: Jeptha Creed Distillery, a family-owned operation. The Nethery family takes a farm-to-bottle approach and grows the heirloom “Bloody Butcher” red corn used in its products on its 1,000-acre farm and sources other ingredients as close to home as possible. After testing the red corn, mother and daughter distillers Joyce and Autumn decided to use it more extensively in their products. “Bloody Butcher gives a flavor you can’t get from yellow corn; it has more fruity notes,” says Autumn, one of the youngest distillery owners in the U.S. Take a guided tour of the distillery and you’ll get to see all phases of production up close, ask questions, plus warm your palate tasting bourbon, moonshine and vodka. During winter months, you can also visit the on-site bar Thursdays through Sundays to savor seasonal cocktails like the Bloody Butcher Mary, Pumpkin Pie Martini, and Harvest Cider among other delicious concoctions made blending Jeptha Creed products and seasonal ingredients.

Prefer to walk with bags in hand? Shop ‘til you drop at The Outlet Shoppes of the Bluegrass, the only designer outlet shopping center in the state of Kentucky. Save 20 to 70 percent off at retailers like Gucci, Michael Kors, Kate Spade, Tommy Hilfiger, Calvin Klein, Polo Ralph Lauren, Vera Bradley, and more. Head to historic downtown Shelbyville (also known as Shelby Main Street) to shop the eclectic mix of dozens of one-of-a-kind boutiques like Needle Nest (which specializes in counted cross-stitch and needlepoint) and Polka Dotted Pineapple (where you can find some of the showy hats popular at the Kentucky Derby). Don’t miss Wakefield-Scearce Galleries at historic Science Hill which houses one of the world’s largest antique silver collections as well as one of the nation’s largest collections of antique English furniture and antique home décor including paintings, chandeliers, architectural elements, and more eye-pleasing accessories.

Warm yourself from the inside out with steaming plates of unforgettably scrumptious food. Three of the season’s hottest restaurants in Shelbyville have deep historic roots. The cold-weather menu at The Red Lion, a cozy new pub located in a former laundry room at what was the Science Hill school from the late 19th to early 20th centuries, features comforting favorites like a jumbo pretzel and beer cheese dip, fried catfish with house-made potato chips, Shepherd’s Pie, jerk chicken, fried green tomato lasagna, and a six-ounce Angus patty-melt burger smothered in Guinness caramelized onions and cheddar. Grab a table near the fireplace if you’re battling chills. For an authentic taste of renowned Kentucky classics, don’t miss Claudia Sanders Dinner House. The restaurant was opened by Colonel Harland Sanders and his wife Claudia after Kentucky Fried Chicken was sold. All these years later, fried chicken is on the menu alongside options like Kentucky Hot Brown, sugar cured ham and biscuits, Kentucky club sandwich, chicken and dumplings soup, pork chop sandwich and other stick-to-your-ribs favorites. The Old Stone Inn & Tavern, newly opened in a building constructed in 1792, is run by Chef David Danielson, who gained notoriety running the kitchen at Churchill Downs and serving as a celebrity judge on Bravo’s Top Chef. Inspired by local seasonal products, his Tavern menu features Southern favorites like grit fritters, deviled eggs, and shrimp & grits as well as creations like goat cheese and beet ravioli, winter salad with grilled chicken, and whole hog fried bologna.

Pull a warm blanket up to your chin and snuggle in for the night, whether you prefer a cozy room or elegant suite. Shelbyville has a roster of five familiar brand-name hotels including the Holiday Inn Express and brand new Hampton Inn, plus quaint inns like the Yellow Carriage House Bed & Breakfast, a 1890 home updated with modern amenities including soaking tubs, and Walnut Grove Farm, where lodging is in a converted dairy barn. You can also find several Airbnb options that range from whole-house rentals to lofts. Popular favorites include the spacious Loft on Main, which sleeps six and has two fireplaces in the large great room, the stylish Urban Loft Downtown that sleeps 16 and is so high-end it’s been featured in magazines and on TV, and the Saddlebred Suite with incredible views of historic Shelbyville.

For more information contact the ShelbyKY Commission & Visitors Bureau at 502-633-6388 or VisitShelbyKY.com.

ShelbyKY Tourism Commission & Visitors Bureau

1011 Main St.
Shelbyville, KY 40065
(502) 633-6388