ShelbyKY (Simpsonville, Shelbyville and Shelby County, Kentucky) has become a hit destination amongst shoppers looking for the perfect gifts during the holiday season. As the home of Kentucky’s only designer outlet mall and with a bevy of popular boutique shops, many people will make a trip here in the coming weeks to cross items off their gift lists.

While you’re spending your time here, you’ll definitely need to eat, you may need to entertain your kids, and you may decide to do some of the fun activities that bring visitors just like you from across the globe to ShelbyKY. This guide will help you plan out a day in both Simpsonville and Shelbyville to maximize your time here.

Planning A Day in Simpsonville

Because of The Outlet Shoppes of the Bluegrass, Simpsonville is an enticing place to visit on Black Friday. The deals found in the various stores that day are extraordinary, making it an imperative stop for many shoppers. Before you make your excursion there, fuel up for the shopping rush with a coffee and a snack from Next Step Cafe. 

This quaint little coffee shop will put you in a good mood thanks to the taste of everything they serve, but also because it helps people with high-functioning autism get a better idea of how they want to spend their career. The internship program they complete also allows them to create clothes, jewelry and knick-knacks that are for sale in the cafe lobby, too. These could make for excellent stocking stuffers! 

After a big morning of shopping, make your way back to downtown Simpsonville for lunch at Weathered Oak Farms. Their famous Pop’s Sourdough makes for delectable cinnamon rolls and fantastic sandwiches. Pair either of those with coffee, hot cocoa, lemonade, or iced tea and you’ll be recharged for a big afternoon.

The afternoon spree can start right next door with a visit to The Lovely Fig, where you’ll find wonderful clothing, jewelry and items for home. Little Mount Lavender, which is located just across the street, has an abundance of products that center around, you guessed it, lavender. Soaps, candles, pet goodies, plants and more can all be purchased here. Don't forget to get a snack from their bakery or indulge from their restaurant, either.

After that would be a great time to entertain your kids, and you can begin by visiting the recently opened Story Nest KY. Featuring books designed to stimulate a child’s imagination, sweets that kids can take pride in buying themselves, and a play area, this is a great spot to let them entertain themselves and pick up a book as a gift for them when they’re distracted.

Books at the Story Nest

Five minutes away, young girls are in for a treat if you book an appointment to Maple Lane Nursery. This cute building that looks like a dollhouse from the outside allows girls the chance to adopt a baby doll. With a personalized process that leaves each visitor assured they’re selecting the right baby, they’ll receive an adoption certificate, some essential caretaking items, and the chance to buy accessories for future use, it’s a heartwarming experience that families have quickly flocked to in a half-year of being open.

By now, it’s time for dinner, and nothing seals the deal on a day of fun quite like pizza. Especially when it’s deep-dish that tastes like it’s from Chicago, which is what you get at Chi-Pie. There’s also a thinner tavern-style pizza available, plus sandwiches, soups, a full bar, and tasty desserts. 

With a trunk full of great gifts and excellent meals consumed, you’ll leave Simpsonville fulfilled and ready to take on its neighbor to the east, Shelbyville.

Planning a Day in Shelbyville

While Simpsonville is the best place to be on Black Friday, Shelbyville has an equally good claim for Small Business Saturday thanks to the locally-owned boutiques located here. Before you go to any of them, you need the proper breakfast, of course. Carriss’s Grocery—voted second best breakfast by Kentucky Living readers this year—will set you up for success thanks to their pancakes, hash browns, eggs, grits, gravy and more. The friendly, welcoming atmosphere will be the cherry on top of the experience before you go shopping.

And the Shelby Main Street is the ideal place to go, with many of the shops you’ll want to peruse located here. Among them are The Polkadotted Pineapple, Reclaimed on Main, The Paisley Pig, Pineapple Paisley Boutique, Wakefield-Scearce Galleries, and Honeysuckles Children’s Boutique – just to name several. 

For lunch, you’ve got choices without having to go far. If you’re craving a good sandwich, waltz on over to McKinley’s Cafe. For some traditional American bar food, head to Parlay Sports Bar, Last Stop Brewing, or Convenient Food Mart. If Mexican-inspired fare is calling your name, you have La Cocina de Mama and La Fogata to choose from. Whatever you decide upon, you’ll get a great meal, friendly service, and receive your second wind for the afternoon.

If your shopping to-do list is done, it’s time to have some fun. If the weather’s nice and you want to be active, you could go for a walk at Red Orchard Park or the Greenway Trails. If you’re a hardcore golfer, check out Weissinger Hills Golf Course or Shelbyville Country Club. Those pressed for time given daylight savings ending, or those who are newer to golf, might like Clear Creek Golf Center. If you prefer disc golf, then Ryan’s Course at Red Orchard will get your competitive juices flowing.

Want to be outside and immersed in what Kentucky is famous for? Take a horse farm tour! Numerous options are available, including West Meadow Farm and HorseSensing. You’ll be wowed by the amount of detail that goes into a day at any farm you pick, and who knows? You might be tempted to buy a horse for a loved one for the holidays.

You can also combine shopping and bourbon together by taking a distillery tour at Bulleit or Jeptha Creed. Once you learn about how these fine beverages are made, you’ll have plenty of bourbon, clothes, accessories, and experiences you can shop from for your loved ones at their gift shops. 

Bulleit Bourbon

All that’s left to do is have dinner, and once again, you have options. Italian lovers will love Milano’s, while those seeking a true southern dining experience will sprint to The Bell House (reservations are recommended) or Claudia Sanders Dinner House. If you opted against Mexican earlier in the day but are craving it for supper, Fiesta Mexicana and Mi Casita are another couple of great choices you have.

If you want a big holiday event to be a part of your shopping spree, check out the awesome lineup of festivities happening in November and December. And if you’re seeking out some specific items from the shops listed above and others, keep your eyes peeled for our ShelbyKY holiday gift guide that will be published before Thanksgiving! 

If you’re ready to start planning your trip, our visitor guide can help. It's free and contains wonderful information about the many things to do in ShelbyKY. Click here to request a visitor guide or download a digital copy.