Ah…Christmas in Bluegrass country, the warm and fuzzy feeling that Hallmark movies are made of! Imagine strolling down Main Street with its charming shops decorated with fresh greenery and sparkling lights, popping into a cozy restaurant for lunch or dinner, or browsing through an antique store: that’s Shelbyville.

Kentucky Monthly A Wakefield Christmas
Photo courtesy of Kentucky Monthly magazine.

Shelbyville and its shopping near Louisville, Frankfort, and Lexington, is the perfect center for your search for holiday treasures. Come for the day or plan a pre-holiday Kentucky weekend getaway in the Saddlebred Horse Capital of the World. Whether you’re shopping for the equestrian in your life, an avid outdoors lover, your fashion-forward sister, or a bourbon aficionado, you’ll find something for everyone on your list.

Charming downtown shopping

Take respite from the hustle and bustle and crowds.  Boutiques and specialty shops along Main Street and in downtown Shelbyville feature unique fashion and gifts in an easy-to-shop environment.  Enjoying the festive holiday spirit in Shelbyville is one of the most fun things to do in Kentucky, in keeping with Small Business Saturday on November 26, a nationwide holiday encouraging people to shop small and support local businesses.

A pink dress on a stand with a Derby-style women's hat.At Gypsy Sisters Boutique, you’ll find beautiful, trendy clothing, jewelry, and gifts for both women and men.  Follow them on Instagram @gypsysistersofky and download the free mobile app The Gypsy Sisters for 24/7 access to all fashion lines!

Be sure to stop in the Polka Dotted Pineapple for a great selection of casual and dressy designer and name-brand attire for all ages.  They are known for custom hats and designer dresses for the horse racing crowd as well as upscale consignments. Polka Dotted Pineapple offers a 10% discount for military and first responders – ask the cashier at checkout! 

Honeysuckle's Children BoutiqueFind some of the cutest holiday kids’ fashions and gifts ever!  At Honeysuckles Children’s Boutique, you’ll find that perfect holiday outfit for both boys and girls ranging in size from newborn to size 10.  Honeysuckles is open Tuesday through Friday, 10 AM–5 PM and Saturdays 10 AM–2 PM.

Flowers, plants, and gifts…oh my!  Stop in Pathelen Flower & Gift Shop for a nice selection of plants and flowers, fruit and gourmet baskets, gift baskets, baby gifts, home décor, and so much more. For your holiday table or special event, shop Flowers by Sharon, a family-owned florist for over 40 years, offering the finest floral arrangements and gifts.

ShelbyKY is the place to shop for the equestrian in your life.  Shelby Horse Supply has everything a champion show horse might need. The premiere equine tack and leather store in ShelbyKY has a wide range of products, from saddles to bridles to reins. And you’ll find plenty of gift-ready items there, too, with their selection of boots, belts, keychains, and even dog collars. At The Winners Circle Horse Supply, you’ll find everything from gifts to apparel, footwear, saddles, and everything in between.

The Outlet Shoppes of the Bluegrass

Designer shopping at the best prices

Outlet Shoppes ChristmasWhen you are in the area and looking for things to do near Louisville, be sure to save time on your itinerary for The Outlet Shoppes of the Bluegrass. With over 90 designer and famous brand stores all in one location, you simply cannot go wrong.  The Outlet Shoppes of the Bluegrass is the largest of its kind in Kentucky, and there is literally something for everyone. You can shop until you drop. Designer bags, apparel, shoes, gourmet cookware – you’ll find it here. Black Friday shopping starts bright and early at 6 AM on November 25th! And don’t forget a visit to Santa, who'll be at the Outlet Shoppes of the Bluegrass from December 4th through the 24th.

Be sure to check out some of our places to stay for any special holiday shopping rates.

Give the gift of an experience

A bartender pouring a snifter of bourbon at Jeptha Creed Distillery in Shelbyville, KYWhat says Kentucky better than Bluegrass, Bourbon, and Horses? It's all here in Shelby County, Kentucky. For that very special person – or even yourself! – why not give the gift of a Kentucky Bourbon Trail vacation?  Plan your Bourbon Trail getaway starting with two local distilleriesBulleit Frontier Whiskey and Jeptha Creed Distillery, both near Shelbyville. Shelby County equestrian events and farm tours in the Saddlebred Horse Capital of the World are just a few fun things to do in Kentucky.  There are plenty of places to stay in Shelby County, from charming bed and breakfasts to brand-name hotels, to spectacular vacation rentals, with an impressive selection of places to eat nearby.

Let the Holiday Shopping season begin!