The holiday season is almost upon us, and if there’s anything to know about ShelbyKY (Shelbyville, Simpsonville and Shelby County, Kentucky), it’s that we know how to put the magic in the air this time of year.
Well before presents are unwrapped, numerous events take place across the county to stir up excitement, wonder and joy for people of all ages. If you, your family or your friends are seeking out some holiday festivities, you need to make a trip here to experience these marquee events.
🎅Grand Tree Lighting Celebration
Santa and Mrs. Claus hope to be joined by you and your family on Saturday, November 7 at The Outlet Shoppes of the Bluegrass from 6 to 8 PM for the unofficial kickoff to the holiday season. The merry couple will arrive via a beautiful horse-drawn carriage to light up a tree that stands 32 feet tall! You’ll also be able to get free photos with them, while meeting other famous figures like the Grinch, Cindy Lou from Whoville, and the life-size Polo Ralph Lauren Teddy Bear. All the while, enjoy live musical performances, free Ghirardelli hot chocolate, and a 100% chance of snow… no matter what the weather forecast says, thanks to the magic of the Outlet Shoppes.

While it’s a local favorite, this event is one of the most highly attended events by non-residents each year for good reason. Everyone will descend upon Shelbyville’s historic Main Street for this delightful celebration on Saturday, November 14, from 3 to 8 PM. Enjoy over 100 vendor booths selling a variety of goods, a plethora of food trucks, Santa’s workshop, trolley rides, and live music before the main event — the tree lighting — takes place at 6:30 PM. The outstanding shops and restaurants along Main Street will be open and participating with contests and offering samples as well.

🎨Winter Splendor & Holiday Magic with the Shelby Regional Arts Council
This special art exhibit featuring festive works of art will be displayed at the Dogwood Art Gallery & Studio. An opening reception takes place on Friday, November 13, from 5 to 7 PM. From that point on, the exhibit will be open to the public from 10 AM to 4 PM Tuesday- Saturday until the end of December. If you can’t make it before the calendar turns, you’re in luck! It will continue through the end of January from 10 AM to 4 PM Wednesday-Saturday.

Image courtesy of Shelby Regional Arts Council
If you’d prefer to be making art yourself, you have the opportunity to craft some of your own decorations during this special event hosted by Kentucky Kate Art (Katie Adams). On Sunday, November 15 from 2:30 to 5 PM, you can join her at Shelbyville Country Club. Whether you want to come alone or with some friends, you’ll receive all the materials you need as part of your registration so that you can create something you’ll be able to use for years and years. You may bring snacks and non-alcoholic drinks of your choice as well, just make sure they aren’t so big they’ll get in the way of your creative space.

Image courtesy of Kentucky Kate Art
🎁 Once Upon a Christmas Gift Show
Admittance is free to this local shopping extravaganza takes place on Saturday, November 21 from 10 AM to 3 PM. The first 50 people to enter will receive coupons ranging from $5 to $25 off purchases at this event. More than 60 artisans will be on-hand offering beautifully made goods that you’ll want for yourself, or to gift to a loved one this holiday season. Santa and Mrs. Claus will be back in the area for this event, and will be available for family photos.

Images courtesy of ArtSpark Productions
🎭 It’s A Wonderful Life at the Shelby County Community Theatre
The Shelby County Community Theatre produces a holiday show every December, and this year, it’s a true classic with It’s A Wonderful Life. There will be performances on eight days, beginning with opening night on Friday, December 3 at 7:30 PM. Three of the shows will be matinees, including the curtain call on Sunday, December 13 at 2:30 PM. Tickets go on sale on Thursday, November 12.

Image courtesy of Shelby County Community Theatre
On Saturday, December 5, the official tree-lighting celebration in Simpsonville will take place, amidst a bunch of other family-friendly fun. The event takes place from 3 to 9 PM and will feature a special edition of the Simpsonville Farmers’ Market where you can get locally-made food and other goods from 50+ vendors. Additionally, there will be a parade, complimentary hot cocoa, activities for kids including a spot to write letters to Santa, and much more.

Image courtesy of Simpsonville Parks & Recreation
⛸ Winter Magic at The Outlet Shoppes
Just down the street from downtown Simpsonville on the same day, Winter Magic kicks off from The Outlet Shoppes of the Bluegrass. Each Saturday and Sunday from that point through Christmas will feature a free iceless skating rink — one of the few outdoor skating rinks available anywhere in central Kentucky during the winter! No snow or cold weather is required. All you have to do is show up and be ready to have a blast with your family or friends.

☕️ A Christmas Royal Tea at Wakefield-Scearce Galleries
For the third consecutive year, this event that has quickly become a cherished holiday staple in the community will be held at Wakefield-Scearce Galleries. It takes place on Saturday, December 19 from 12 to 2 PM. When guests arrive in the courtyard, they’ll be served sparkling tea in champagne flutes. The traditional tea service will include loose-leaf teas, sandwiches, baked goods, and sweets. Guests are encouraged to arrive early to admire the beautifully decorated rooms throughout the building and get some last-minute shopping done. Attending this event and others at Science Hill directly supports their mission of providing recovery addiction programs in the area.

It’s going to be a majestic holiday season in ShelbyKY, and there will be plenty more holiday wonder served up over the next several weeks. To stay in the know with all that’s happening, keep tabs of our Event Calendar.
Whether you’re coming to the area to shop for presents, sip bourbon with Santa, or experiencing one of the many festivals, you can start planning your trip with our visitor guide. 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.