Events in Williamsburg, KY

Appalachian Motorcycle Group partners with Harlan KY Tourism for the second annual Bloody Harlan Ghost Ride, a Kentucky haunted fall colors experience that blends scenic mountain miles with chilling local lore. The day centers on riding some of Eastern Kentucky’s most striking routes, including Revenue Runner Highway 92, the Joe C. Paul Medal of Honor Trail, Gateway 119 on the McCoy side, and Coal Train 421. Expect sweeping overlooks, peak foliage, and glimpses of coal mining history before rolling into downtown Harlan. After dinner, local guides lead a Haunted Harlan Ghost Tour that delves into the town’s past, including stories from the Coal Wars and visits to reported paranormal locations such as the Harlan County Courthouse, Sassy Trash, the Historic Harlan Courthouse, and other notable downtown sites. The night continues along 987 Waterside at Martins Fork, a scenic stretch by day that takes on a mysterious character after dark. Riders hear accounts of ghost sightings, Bigfoot encounters, unexplained lights, UFO activity, and enduring Appalachian legends, with stops that highlight why this area is considered a paranormal hotspot. This event marks the final official AMG ride of the Kentucky season. Look forward to memorable mountain riding, vibrant fall color, haunted history tours, plentiful photo opportunities, and welcoming Appalachian hospitality. Costumes are encouraged. Special hotel rates in Harlan are planned to be announced for those staying overnight and enjoying a relaxed Sunday ride home. One ride, one night, and countless stories to tell.

This freezeout poker tournament features a guaranteed prize pool of $12,500 with a $1,250 buy-in. Players start with 100,000 chips and levels last 20 minutes. Initial buy-in is available until the second break, which follows Level 10. At least the top 10 percent of the field will be paid. As a freezeout, there are no rebuys, no re-entry, and no add-ons. Member setup and registration are available before play begins. The guaranteed prize pool is active with a minimum of ten unique registered players.

Celebrate spooky season with a drive-in Halloween movie at Kentucky Splash Waterpark and Campground. The featured film will be announced closer to the event.

Celebrate the newest installment in Sarah J. Maas’s A Court of Thorns and Roses series at a themed release party filled with fae vibes and fandom fun. The evening includes interactive games, food and sweet treats, and exclusive goodie bags. A $50 ticket provides admission to the full event experience along with a hardcover copy of the new release. Capacity is limited for this Prythian inspired celebration.

Celebrate Halloween with activities to enjoy before heading out to trick or treat.

A full band takes the stage at The Mint Gaming Hall - Cumberland in Williamsburg for a live show built around music by The Band, Led Zeppelin, Creedence Clearwater Revival, Sly and the Family Stone, The Allman Brothers, and others. The performance focuses on well known songs from these artists.

This event offers great music, tasty food, and exciting slot action for a simple, feel-good time.

The second annual Christmas in the Park brings an expanded celebration to the Levi Jackson Clubhouse in London, KY. Expect holiday shopping from local vendors, food trucks with plenty of treats, seasonal photo opportunities, and entertainment set within a warm, nostalgic Christmas atmosphere. Families and friends can kick off the season with cheerful activities, tasty bites, and memorable moments.

Celebrate the start of the Christmas season with a Hanging of the Green, marking the beginning of the holidays.

Those who would like to participate in the parade can reach out to Kay Petrey at 606-765-0701 or Jayma Moore at 606-523-8384. Application details will be shared closer to the event.