October brings crisp mountain air and vibrant fall colors to Eastern Kentucky, but it also brings a whole lot of spooky fun! Pikeville and Pike County get into the Halloween spirit with a fantastic lineup of events for everyone. Whether you are looking for family-friendly downtown trick-or-treating, creative fall workshops, classic horror movies, or festive night-out activities, there is something happening all month long. Grab a warm pumpkin drink, put on your costume, and use this guide to plan your ultimate October in the mountains!
Frankie & Wifey Paint Night
Paint your way into Halloween spirit with a little spooky fun at 2 Broke Art Teachers! Paint individually, bring a friend, or make it a date night to create your own “Frankie & Wifey” masterpiece (or choose from other available options)!
📍 Location: 2 Broke Art Teachers (4505 N Mayo Trail, Pikeville, KY 41501)
📅 Date & Time:
- Friday, October 9, 2026, at 5:30 PM
- OR Saturday, October 10, 2026, at 5:00 PM
💲 Cost: $25 per canvas
📋 Details: Open to all skill levels! Other painting options are available. Private message 2 Broke Art Teachers to book your spot! Please include your preferred date and painting choice when messaging.
54th Annual Hal-O-Win
Dress up your little ones and bring them to the 54th Annual HAL-O-WIN for a night of spooky fun! Bring the whole family out for an evening packed with games, contests, food trucks, and the famous Token Hunt with live clues broadcasted on 93.1 WDHR & THE GOAT. Show off your best outfit in the costume contest for a chance to win $50 CASH, brought to you by Community Trust Bank, alongside huge prizes like an iPad, a TV, and more!
Event Overview
- 📍 Location: Mountain Top Media Stage / Appalachian Wireless Arena Plaza
- 📅 Date & Time: Tuesday, October 20, 2026, from 5:00 PM – 9:00 PM
- Games & Contests: 5:00 PM – 7:00 PM
- Token Hunt: 7:00 PM – 9:00 PM
- 💰 Cost: FREE to attend!
- 📋 Details: Open to all kids ages 0–12 in costume with no participant limit!
How to Win Big
- Sign Up for a Game or Contest: Compete for amazing prizes and enter the costume contest.
- Join the Token Hunt: Listen to live clues from the stage and on-air via 93.1 WDHR & THE GOAT to find hidden tokens around town. Find a token, be present, and bring it back to the staff to claim your prize!
- Free Swag: Grab a free, limited-edition HAL-O-WIN T-shirt while supplies last!
Mark your calendars, follow Mountain Top Media for updates, and come join the fun… IF YOU DARE!
Halloween Spooktacular at Breaks Interstate Park
Get ready for a full weekend of family-friendly Halloween fun at the “Grand Canyon of the South”! The annual Halloween Spooktacular is packed with costumes, creativity, storytelling, campsite decorations, and trick-or-treating for all ages.
📍 Location: Breaks Interstate Park (627 Commission Cir, Breaks, VA 24607)
📅 Dates: Friday, October 16 & Saturday, October 17, 2026
📋 Registration: Open to all visitors—start planning your carved pumpkins, costumes, and campsite decorations now!
Friday, October 16 Schedule
- ⏰ 7:00 PM: Pumpkin Judging Contest (Bring your pre-carved or pre-decorated pumpkin!)
- ⏰ 7:30 PM: Spooky Storytelling at the Amphitheater
Saturday, October 17 Schedule
- ⏰ 11:00 AM: Children & Pets Costume Judging Contest (Amphitheater)
- ⏰ 1:30 PM: Campsite Decorating Contest Judging
- ⏰ 4:00 PM: Buses & Shuttles depart for Campground Trick-or-Treating
- ⏰ 6:30 PM: Buses & Shuttles begin return trips to the parking area
Trick-Or-Treat at MineShaft Harley-Davidson
Rev up your Halloween spirit with a afternoon of sweet treats and spooky fun at MineShaft Harley-Davidson! Bring the whole family out for trick-or-treating packed with lots of goodies, candies, and free hotdogs for everyone to enjoy. Show off your best outfit in the costume contest starting at 3:45 PM!
📍 Location: MineShaft Harley-Davidson (114 Harley Dr, Pikeville, KY 41501)
📅 Date & Time: Saturday, October 17, 2026, from 2:00 PM – 4:00 PM (Costume contest begins at 3:45 PM)
📋 Details: Free and open to all trick-or-treaters! For questions or more information, call (606) 433-0911.
The Rocky Horror Picture Show at The Appalachian Center for the Arts
A favorite cult classic returns to downtown Pikeville! As part of The APP’s cult classic movie series, this annual screening invites fans for an unforgettable night of high energy, outrageous characters, and timeless rock ‘n’ roll music. Follow a newly engaged couple who stumble into the bizarre world of Dr. Frank-N-Furter after their car breaks down on a rainy night. Whether you know every line by heart or are experiencing it for the first time, get ready for a wild and memorable night out!
- 📍 Location: Appalachian Center for the Arts (218 2nd St, Pikeville, KY 41501)
- 📅 Date: Saturday, October 17, 2026
- ⏰ Time: 7:30 PM
- 🎟️ Tickets: $20 per guest (plus a $2.50 processing fee per ticket; all sales final)
- 🔞 Age Limit: Rated R (18+ only)
- 📋 More Info & Booking: Get tickets online at www.theapparts.org or call 606-262-4044.
16th Annual Nightmare on Main in Pikeville
Get ready for an evening packed with community spirit and spooky fun right in the heart of downtown Pikeville! Whether you’re dressed up as a little witch, a friendly ghost, or your favorite superhero, Nightmare on Main is a can’t-miss family event filled with costumes, candy, and Halloween cheer for all ages.
- 📍 Location: Main Street, Downtown Pikeville
- 📅 Date: Thursday, October 22, 2026
- ⏰ Time: 6:00 PM – 9:00 PM
Family Friendly Spooky Fun at the Appalachian Center for the Arts
The Appalachian Center for the Arts presents a weekend of Family Friendly Spooky Fun featuring classic Halloween movie screenings and festive activities for the whole family! Enjoy double the magic with Disney’s Hocus Pocus and Tim Burton’s The Nightmare Before Christmas, plus costume contests, photo ops, sweet treats, and more!
Event Overview
- 📍 Location: The Appalachian Center for the Arts, 218 2nd St, Pikeville, KY 41501
- 📅 Movie Screenings:
- Disney’s Hocus Pocus: Friday, October 23 at 7:30 PM
- Tim Burton’s The Nightmare Before Christmas: Saturday, October 24 at 7:30 PM
- 📞 Contact: (606) 262-4004
- 🌐 Website: www.theapparts.org
Activities & Attractions
- Costume Contests
- Oogie Boogie Bar
- Photo Ops
- Potion Making
- Sweet Treats
Spooky Science at Pike County Public Library
Explore the eerie side of science! Kids and families can discover how mystery matter leaves a bloody handprint, create haunted chemical reactions to send ghosts soaring, make floating eyeballs, and release a monster from a jug with spooky energy. Best of all, this hands-on event is completely free!
- 📋 Registration: No registration required! Just show up at your local library.
Locations & Times:
- 📍 Pike County Public Library (126 Lee Ave, Pikeville, KY)
- 📅 Friday, October 23 | ⏰ 4:30 PM
- 📍 Belfry Public Library (22 Western Ave, Belfry, KY)
- 📅 Saturday, October 24 | ⏰ 1:00 PM
- 📍 Phelps Public Library (38575 KY-194, Phelps, KY 41553)
- 📅 Saturday, October 24 | ⏰ 3:00 PM
- 📍 Elkhorn City Public Library (170 W Russell St, Elkhorn City, KY)
- 📅 Saturday, October 24 | ⏰ 5:00 PM
Spring Branch Events Haunted House
Brace yourself for even bigger scares as Spring Branch Events returns for its second annual Haunted House—now double the size of last year! Enjoy on-site concessions and grab spooky photo opportunities with horses while you wait to brave the walk-through.
📍 Location: Spring Branch Farm (36 Spring Branch, Pikeville, Ky 41501)
📅 Dates & Times: October 23, 24, 30 & 31 | 8:00 PM – 12:00 AM
📋 Admission: Cash only at the door — $15 Adults | $5 Children (12 and under)
Spooky Circus Tales
Get ready for an unforgettable evening of Halloween magic behind the Pike County Public Library! Night Owl Circus Arts is putting on a fantastic, free show packed with incredible aerial acrobatics, dazzling juggling, and whimsical ghost stories. Gather the family and head over on Tuesday, October 27 at 5:30 PM—no sign-ups needed!
📍 Location: Pike County Public Library (126 Lee Ave, Pikeville, KY)
📅 Date & Time: Tuesday, October 27 at 5:30 PM
📋 Admission: Free (No registration required)
KSP Post 9 Trunk or Treat
Rev up your Halloween spirit with an evening of sweet treats and spooky fun at Coal Run’s Spooktacular Bash in the Park! Bring the whole family out for a double-feature event packed with free face painting, a balloon artist, hayrides, and free hotdogs for everyone to enjoy. Start with trunk-or-treating at KSP Post 9, then head over to the park to cap off the night with a free movie under the stars!
📍 Location: Coal Run City Park (Coal Run, KY)
📅 Date & Time: Tuesday, October 27, 2026, starting at 5:00 PM (Sensory Hour begins at 4:30 PM at the park)
📋 Details: Free and open to all trick-or-treaters!
Trick-or-Treating in Pikeville, Kentucky
Bring out the little ghosts, goblins, superheroes, and princesses for a sweet night of Halloween excitement! The City of Pikeville invites families to walk neighborhood streets, fill up candy bags, and make happy autumn memories in a fun, safe environment.
- 📍 Location: Neighborhoods across the City of Pikeville
- 📅 Date: Thursday, October 29, 2026
- ⏰ Time: 6:00 PM – 8:00 PM
- 📋 Costumes & Buckets: Grab your favorite costume, bring a sturdy candy bag, and enjoy safe street trick-or-treating with the whole family!
Shelby Valley Volunteer Fire Department Haunted House
Get ready for spine-chilling thrills for all ages as the Shelby Valley Fire Department turns Station One into a haven of horrors! Packed with hard-earned scares built by local firefighters, this seasonal favorite also features delicious concessions like apple pies, caramel apples, hot dogs, and hot chocolate. If you drive by and see the red light flashing, the doors are open!
- 📍 Location: 55 Douglas Parkway, Pikeville, KY 41501
- 📅 Date: Every October Weekend
- ⏰ Time: 8:00 PM – 12:00 AM
- 📋 Details: Open to all ages—come support your local fire department and kick off a great Halloween tradition!
Stop by the Pikeville-Pike County Welcome Center
Planning your October trip or looking for local recommendations? Be sure to drop by the Pikeville-Pike County Welcome Center in downtown Pikeville for any help with local maps, brochures, event guides, and personalized tips to make the most of your Halloween weekend in the mountains.
- 📍 Location: Pikeville-Pike County Welcome Center (685 Hambley Blvd, Pikeville, KY 41501)
- ⏰ Hours:
- Monday – Friday: 9:00 AM – 5:00 PM
- Saturday: 9:00 AM – 3:00 PM
- Sunday: Closed
- 📞 Phone: Call 606-432-5063 for info or questions before your trip!
