Fall Festivals in the Bluegrass

FRI OCT 1 (thru OCT 3)

Oktoberfest Harrodsburg 2021 is celebrating its fifth year: free concerts on Main Street all weekend long; German fare and festival style treats; artists and vendors; family fun at the Carnival and Kinderland area.

Mt. Sterling Fly-In/Drive-In Breakfast and Aviation Day. Breakfast starts at 7 am and ends around 11 am. Pilots flying in receive free breakfast. Main activities start around 9 am and end around 4:00 pm. Airplane rides are offered for a minimal charge, plus a candy drop for the kids, food and other various vendors and many fun activities for the whole family. Bring your lawn chair. Free Parking.



Wilmore’s 23rd premier arts and crafts festival celebrates “Meet Me at the Tracks” with more than 50 vendors with an array of juried art and hand made crafts. Explore downtown boutiques and shops along with live entertainment and refreshments.

Winchester Downtown Arts Festival, 9 am to 4 pm.



South Elkhorn Fall Festival, 9 am to 4 pm, 4343 Harrodsburg Road, featuring arts, crafts, food, live music, and handcrafted goods of all kinds.


FRI OCT 15 (thru OCT 18)

Kentucky’s Oldest Festival is Court Days, dating back to 1794 in Downtown Mt. Sterling! Hundreds of vendors will offer a huge variety of merchandise and food for four days. Enjoy fun entertainment — including live music and the Mt. Sterling Mullet Contest. Vendor and Visitor information at www.mtsterlingtourism.com.


Happy Halloween, Hamburg! 

Whether you’re in the mood for a Halloween High Tea or a Murder Mystery dinner, Lexington has something for everyone this Halloween Season.

Below is a sampling of area attractions. All dates and programs are subject to change. Check with individual venues to confirm.



Adventure Theatre Presents: Frankie Stein’s Halloween Extravaganza (murder mystery dinner theatre) at Shaker Village. “After flunking out of med school, Frankie Stein is pursuing his passion for television by hosting a Halloween-themed game show with a Bill Nye twist and a dash of Martha Stewart.”



Fort Boonesborough State Park (Richmond) will offer a Halloween Lights Drive Thru, beginning Friday October 8 and continuing through Saturday October 23.



Join the Lexington Paranormal Investigation Society as they dive into the spookier side of White Hall. Experienced investigators will guide you through the steps of completing your own paranormal investigation as you tour the mansion and learn more about its past residents.



Trunk or Treat at Bi-Water Farm will include Hayrides, Mega Slide, Sunflower Field, Pumpkin Warrior Obstacle Course, Ziplines, Corn Maze and more.



Scarefest returns to Lexington Center for the weekend.

Cynthiana hosts “Witches Night Out.”  Calling all warlocks and witches. Grab your favorite witchy wardrobe and head to the streets of Cynthiana, where there will be shopping specials with local boutiques, tarot readings, ghost walks, and more.


ThrillerParade-HJ-PaulMartinSUN OCT 24

Thriller Halloween Parade returns to downtown Lexington.



Wildside Winery will present an evening of wine and cookies with The Cheerful Baker. Each ticket includes a glass of wine or beer or soft drink and everything that you need to make and take home a set of cookies.



The Kentucky Castle will host a Murder Mystery dinner on Halloween Eve. The evening begins in the Grand Ballroom with a cocktail reception and the opening act of “A Deadly Journey,” the evening’s entertainment, which tells the story of the murder of Victor Marshall, a 1940s Hollywood Film Director.

Dress up in your favorite costume and join White Hall State Historic Site for a Halloween High Tea — an evening of thrills, chills, and tea refills. Enjoy a high tea complete with Halloween-themed food, spooky stories, and maybe a surprise or two.


Halloween Fun Runs

OCT 23    Run for the Pumpkins 4-miler, Harrodsburg

OCT 29    The Black Cat Chase 5k, Frankfort

OCT 30    Kiwanis Halloween 5k, Shaker Village

OCT 30    Monster Dash 5k, Danville


This article also appears on page 10 of the October 2021 print edition of Hamburg Journal.

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