Ice Skating Rink
2025-12-05 15:00 - 22:00, 2025-12-06 11:00 - 22:00, 2025-12-07 14:00 - 18:00 (America/Kentucky/Louisville) | Pikeville City Park, 101 Cumberland Ct,, Pikeville, KY, 41501
Get ready to glide into the holidays! The Winterfest Simulated Ice Skating Rink is OPENING SOON at Pikeville City Park!Lace up those skates and make some magical memories with the whole family. Whether you’re a seasoned skater or trying it for the first time, join us for some festive fun! Dates: November 29 – December 31 Location: Pikeville City ParkHours Opening Weekend:Saturday: 11 AM – 10 PMSunday: 2 PM – 6 PM Admission (includes skate rental!):Adults: $10/hrChildren 6 & Under: $6/hrPLUS! Look out for Carriage Rides and the Whitewater Shrine Mini-Train Rides on select dates!Come create your perfect winter moment in Pikeville! We can’t wait to see you there!

Chess Club: Beginner's Theory
2025-12-05 16:00 - 17:00 | Pike County Public Library, 126 Lee Avenue, Pikeville, KY, 41501, United States
New to chess? Learn the basics of the game in a fun, beginner-friendly setting!

We’ll cover piece movement, rules, simple tactics, and opening strategies to help you build a strong foundation. No experience needed!
Meets alternating Fridays at 4:00 at the Pike County Public Library (Lee Avenue).

Carriage Rides
2025-12-05 16:00 - 20:00, 2025-12-06 16:00 - 20:00 | Downtown Pikeville, Pikeville, Ky, 41501
We are pleased to announce that carriage rides will be offered this Friday and Saturday from 4-8.Guests can enjoy a relaxing, scenic ride for $15 per person.This is a wonderful opportunity for families, couples, and individuals to experience a charming and traditional carriage outing.We look forward to providing you with a memorable and enjoyable experience.Call and book with us at 606-794-9881

Whimsical Winterfest
2025-12-05 17:00 - 22:00, 2025-12-06 10:00 - 20:00 | Appalachian Wireless Arena, 126 Main Street, Pikeville, Ky, 41501
Whimsical Winterfest Craft & Gift Fair

Sound of the Seasons
2025-12-05 18:00 - 20:00 | Pikeville United Methodist Church, 107 Main St,, Pikeville, KY, 41501, United States
Free Concert

Ornament Night at Hope Haven
2025-12-05 18:30 - 20:30 | Hope Haven Boutique, 1946 South Mayo Trail,, Pikeville, KY, 41501, United States
Let’s kick off the Christmas season with creativity, cocoa, and community!
Join us on Friday, December 5th at 6:30 PM for a fun night of crafting beautiful Christmas ornaments and enjoying sweet fellowship.
Includes 2 ornaments & refreshments
All supplies provided
Sign up in-store or message us on Facebook
All participants receive a 10% off coupon for Hope Haven!
Let’s create, connect, and celebrate the true JOY of the season — together!

Annie The Musical
2025-12-05 19:30 - 21:30, 2025-12-06 19:30 - 21:30, 2025-12-07 15:00 - 17:00 | Appalachian Center for the Arts, 218 2nd St,, Pikeville, Ky, 41501
With equal measures of luck and positivity, little orphan Annie charms everyone’s hearts despite a next-to-nothing start in 1930s New York City. She is determined to find the parents who abandoned her years ago on the doorstep of a New York City Orphanage that is run by the cruel, embittered Miss Hannigan.
With the help of the other girls in the Orphanage, Annie escapes to the wondrous world of NYC. In adventure after fun-filled adventure, Annie foils Miss Hannigan’s evil machinations… and even befriends President Franklin Delano Roosevelt!
She finds a new home and family in billionaire, Oliver Warbucks, his personal secretary, Grace Farrell, and a lovable mutt named Sandy.
Tickets:
In Advance: Adult: $20 | Kids (up to 18) | Seniors (65+) $13
At Door: Adult: $22 | Kids (up to 18) | Seniors (65+) $15

Dalton Moore
2025-12-05 19:30 - 22:30 | Bank 253, 253 2nd St,, Pikeville, KY, 41501, United States
@Bank253

Christmas giveaway
2025-12-06 | Pikeville YMCA, 424 Bob Amos Dr,, Pikeville, Ky, 41501
For children ages 0-16

Story Time
2025-12-06 11:00 - 12:00 | Pike County Public Library, 126 Lee Avenue, Pikeville, KY, 41501, United States
Story Time is for children ages 5 and under and features books, action/movement, songs, and a craft. Story Time is held Thursdays at 11:00 and 2:00 and Saturdays at 11:00.

Besides being fun, Story Time also helps develop early literacy and school readiness skills through reading, singing, listening, playing, and social interaction. This program lasts approximately 30 minutes, and caregivers and children are encouraged to linger in the library afterwards to further socialize and choose books to take home.

Story Time begins the first week of September and ends the first week of May.

Quilters Group
2025-12-06 11:00 - 13:00 | Pike County Public Library, 126 Lee Avenue, Pikeville, KY, 41501, United States
Pike County Public Library Quilters Group is a quilting social that also teaches quilting and needlework. Participants exchange patterns, quilting ideas, and sewing projects.

Both beginners and experienced quilters are welcome! Quilters Group meets alternating Saturdays at noon at the Pike County Public (Lee Avenue) Library.
No registration required.

FAMILY PAINT CLASS
2025-12-06 13:00 - 15:00 | 2 Broke Art Teachers, 4505 Weddington Square,, Pikeville, KY, 41501, United States
FAMILY PAINT CLASS — PICK YOUR PAINTING! 2 Broke Art Teachers — Pikeville, KYJoin us Saturday, Dec. 6, 2025 @ 1:00 PM for a fun-filled Family Paint Class!Everyone gets to choose their favorite design from the 9 adorable Christmas options! Only $20 each All ages welcome No drawing required — canvases are pre-sketched! Perfect for a holiday family outingPrivate message your number choice to reserve your seats!Seats fill fast—don’t wait!

Snowman Cozies
2025-12-06 16:00 - 17:00 | Pike County Public Library, 126 Lee Avenue, Pikeville, KY, 41501, United States
Join us to make your own adorable Snowman Cozy, complete with a soft towel “blanket,” felt scarf, and festive embellishments. All materials are provided. Registration required.
This program will be held Saturday, December 6th at 4:00 at the Pike County Public Library.
Register here: https://informationplace.libnet.info/event/15085447

Mountain Top Media’s FIRST-EVER Blizzard Bash!
2025-12-06 16:00 - 18:00 | Mountain Top Media Stage, 126 Main St,, Pikeville, KY, 41501, United States
Get in the Christmas spirit with us as we kick off December Mountain Top style!
• Saturday, December 6th• 4–6 PM• Mountain Top Media Stage – 130 Main Street, Pikeville, KY 41501
What’s happening:• Take-Home Prizes• Ugly Sweater Contest – brought to you by Lance Lykins at Walters Toyota Nissan!If you need a car, call 606-356-6940.• Gift Wrapping Race – brought to you by 5.0 Detailing of Raccoon (606) 213-3382
And y’all don’t run off after the fun…The Pikeville Christmas Parade starts at 6 PM right after the Blizzard Bash! You can watch or listen to the parade on 93.1 WDHR, brought to you by The City of Pikeville.
We’ve got more to announce, so make sure to hit Interested or Going to stay updated on the first-ever Mountain Top Media Blizzard Bash!

Merry on Main
2025-12-06 17:00 - 21:00 | Downtown Pikeville, Pikeville, Ky, 41501
Who is READY to Sip, Shop & Save Downtown?Go ahead and tag your shopping buddies, friends and family!The first 100 guest to visit The Shoppes at 225 on Saturday may purchase a Red Bag with exclusive coupons, $10 Downtown Dollars and more!Join us for a MeRrY mix of savings and seasonal cheer—your perfect excuse to shop local and celebrate! Date: Saturday, December 6 Location: Downtown Pikeville Tag your shopping squad and make it a holiday to remember!

Pikeville Christmas Parade
2025-12-06 18:00 - 20:00 | Downtown Pikeville, Pikeville, Ky, 41501
Get ready to spread some serious holiday cheer! The City of Pikeville is looking for festive floats, merry marching bands, local groups, and businesses to be a dazzling part of the 2025 Christmas Parade!

Join us as we light up the night on Saturday, December 6th at 6 PM! This is your chance to showcase your organization to the entire community—and the best part? There is NO registration fee to apply!

When: Saturday, December 6, 2025 at 6:00 PM

Where: Downtown Pikeville, KY

Cost: FREE to apply and participate!

Ready to join the parade? Find the application under the ‘Events’ tab at www.VisitPikeville.com or apply directly here: https://bit.ly/VisitPikeville

Let the mountains move you to make this the best parade yet!

Dixie Lynn
2025-12-06 20:00 - 22:00 | Bank 253, 253 2nd St,, Pikeville, KY, 41501, United States
@Bank 253

UPIKE Music Annual Christmas Concert
2025-12-07 16:00 - 18:00 | UPIKE’s Booth Auditorium, 147 Sycamore St, Pikeville, KY, 41501, United States
Tis the season!
The UPIKE Music Program is proud to present our annual event of the holiday season, the Annual Christmas Concert! Join us for an evening of festive music that you know by heart, including some of your favorite sacred hymns and classic holiday hits!
Our Bluegrass Ensemble will be having a pre-show in the Booth Auditorium lobby at 3:30, so be sure to arrive early to enjoy Christmas carols with a bluegrass twist!
Admission is FREE

Music Theory for Homeschoolers
2025-12-08 14:00 - 15:00 | Pike County Public Library, 126 Lee Avenue, Pikeville, KY, 41501, United States
Understanding how music works will give you the tools you need to write riffs, songs, and solos, and learn to improvise in a friendly hands-on environment.

Class is held every Monday at the Pike County Public Library (Lee Ave) at 2:00.
No previous knowledge of music theory or reading music is necessary, but this class is for students who already know how to play a little bit.

Alibis at The Book Club
2025-12-08 17:00 - 18:00 | Pike County Public Library, 126 Lee Avenue, Pikeville, KY, 41501, United States
Alibis at The Book Club meets every other Monday at the Pike County Public Library (Lee Avenue). Join us for mystery, thrills, and lively discussion!

City Commission Meeting
2025-12-08 18:00 - 19:00 | Pikeville City Hall, 243 Main St #1786,, Pikeville, KY, 41501, United States
6pm @ City Hall

Christmas Music
2025-12-09 11:00 - 12:00 | Pikeville Medical Center, 911 S Bypass Rd,, Pikeville, KY, 41501, United States
Make plans to join us for Christmas Music in the Atrium, a holiday tradition at Pikeville Medical Center! Throughout the month of December, a variety of performers will bring the sounds of the season to our patients, staff and visitors.

ASL Class Movie Night
2025-12-09 16:45 - 18:30 | Pike County Public Library, 126 Lee Avenue, Pikeville, KY, 41501, United States
Join us as the Intro to Sign Language class presents a special screening of CODA! Enjoy this inspiring film and learn more about Deaf culture and communication.

Christmas Ornament Workshop for Kids
2025-12-09 17:00 - 18:00 | Pike County Public Library, 126 Lee Avenue, Pikeville, KY, 41501, United States
Stop by for a fun, hands-on holiday craft! Kids can visit different stations to make quick and easy DIY ornaments to take home. All supplies provided—no experience needed!
This program will be held Tuesday, December 9th at 5:00 at the Pike County Public Library. No registration required.
