It’s that time of year again – when Frankfort transforms into Halloweentown. Throughout October, leading up to the big night itself, all sorts of merry mayhem will make for a spookily good time. So, don your costume and join us for Halloween, Capital City style.
The Gray Lady Tour
Want a ghost tour with a dollop of history? Don’t worry – it’s not the kind you find in the classroom. This is history embroidered with the supernatural.
For more than 200 years, a mysterious lady dressed in gray has been in residence at Frankfort’s most historic home, Liberty Hall. Although no one claims to have met her, many have seen her – peeking from the window of the upstairs bedroom she once occupied as a guest.
Discover her spooky story (and also hear other ghost stories and learn about the history of mourning practices through the ages) every Wednesday throughout the month, with a bonus tour scheduled for Saturday, October 25th.
See why Liberty Hall has become a featured site on the state’s “Kentucky After Dark” tour.
The tours (7:30 – 9:00 p.m.) begin at the Orlando Brown House and include Liberty Hall and its historic garden.
October 8, 15, 22 and 25.
Russ Hatter’s Murder and Mayhem Tour
Now, there’s a phrase designed to freeze the blood. For a city its size, Frankfort has had plenty of both murder and mayhem. Find out about both on a walking tour led by Eleanor Hasken-Wagner, director of the Capital City Museum and host of the podcast Kentucky Deceased.
The two-hour walking tour (7:30-9:30 p.m.) will focus on the city’s mobs, mysteries and murders (including that of the only U.S. governor ever to be assassinated while in office).
Please be forewarned – the gruesome nature of this tour makes it not appropriate for those 15 and younger, and even those under 18 need to be accompanied by a legal guardian. (Now, come enjoy yourself exploring Frankfort’s dark past.)
October 9, 23, 30
Witches Night Out
Whether you want to channel your inner Glenda, the Good Witch or Maleficent, the embodiment of evil; if you and your mother want to dress up as Bewitched’s Samantha and Endora (nose twitching encouraged) or if you choose to grab your two best friends and go as the trio of witches in Shakespeare’s MacBeth, you will have a “bewitching” time at what has become one of Frankfort’s most popular Halloween events.
This is the only night of the year when being “witchy” will get your preferential treatment at all of the city’s shops, bars and restaurants.
October 10
Haunted by History
It seems you just can’t get away from history in Kentucky’s capital. On four nights in October, the Kentucky Historical Society will present a one- hour (7:00-8:00 p.m.) journey into the darker side of that history.
Taking place at the Old State Capitol, the tour will focus on undesirables such as the vengeful star-crossed lovers whose exploits led to tragedy; a murderous gang whose threats and “explosive” behavior terrified the city, and that governor we met earlier whose murder happened right here on these grounds (along with the deaths of two others on the building’s Senate floor).
This one’s not for the faint of heart.
October 17, 23, 24, 30
Haunting on the Hill’s Tour of the Battle of Frankfort
The year is 1864 and the occasion is the Civil War’s Battle of Frankfort where local militia, from their defensive position on Fort Hill, thwarted the efforts by Confederate General John Hunt Morgan to destroy the city.
Every October, people remember the event by hiking the ¾ mile trail used by the defenders to reach the top.
You may or may not encounter the ghostly presence of those defenders, but we promise you will get a workout and a beautiful view.
The historical hike is an afternoon event (3:00-5:00 p.m.), but you can come back that evening (7:00-10:30 p.m.) for the non-historical Spooky Vibes Only event at Leslie Morris Park at Fort Hill.
October 18
2025 Black Cat Chase
Round out the month’s activities with this year’s version of the Black Cat Chase, an annual 3K run/walk sponsored by Frankfort Regional Medical Center.
Costumes are encouraged and Halloween music will fill the air. Bringing your pet black cat to chase is optional.
October 24
With all the activities scheduled, October in Frankfort is looking to be more treat than trick.
