Events in Paintsville

Paintsville’s Events and Entertainment

What’s Happening in Paintsville

Local Events

From tourism highlights to community gatherings, this is where you’ll find events happening around Paintsville. Our calendar is growing, and we’re committed to keeping it updated with festivals, performances, local happenings, and family-friendly events throughout the year. Check back often!

team kentucky department of tourism

Front Porch Pickin’Weekly

Feel the rhythm of Appalachia every Thursday night in Paintsville. Join us each week for Front Porch Pickin’, a beloved Eastern Kentucky tradition held at the iconic US 23 Country Music Highway Museum. Beginning at 7 PM every Thursday, this weekly gathering brings together local musicians, visitors, and music lovers for an unforgettable evening of […]
30 Apr
7:00 PM - 9:00 PM
US 23 Country Music Highway
120 Stave Branch Rd, Staffordsville, KY 41256
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Paintsville Spring Fling 2026

Spring is coming to the mountains, and downtown Paintsville is ready to celebrate. Join us May 8–9, 2026 for the Paintsville Spring Fling, a full weekend of music, food, shopping, and family fun in the heart of town. Main Street, Court Street, and the city parking lot will come alive with vendors, live entertainment, and […]
08 - 09 May
All Day
Downtown Paintsville
Paintsville, KY
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Paintsville ParaConn 2026

Step into the unknown at one of the biggest paranormal events in Eastern Kentucky. Join us on Saturday, June 27, 2026, for Paintsville ParaConn, an unforgettable day filled with paranormal investigations, ghost stories, haunted vendors, and special guest speakers at the Paintsville Recreation Center. Whether you’re a longtime believer, a curious skeptic, or simply looking […]
27 Jun
12:00 PM - 7:00 PM
Paintsville Recreation Center
232 Preston St, Paintsville, KY 41240
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Keith Age Live Paranormal Investigation at the Stafford House

Step inside one of Paintsville’s most historic homes for an exclusive overnight paranormal investigation. On June 27, 2026, legendary paranormal investigator Keith Age will lead a live, hands-on investigation inside the historic Stafford House from 10:00 PM to 1:00 AM. This is not a lecture and not a simple walkthrough. This is a real overnight […]
27 Jun
10:00 PM - 10:00 PM
The Historic Stafford House
102 Broadway Street, Paintsville, KY, United States, Kentucky
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41st Annual Van Lear Town Celebration

Mark your calendars for Friday, July 31 and Saturday, August 1, 2026, and come enjoy two days of hometown fun, music, food, and family-friendly activities as the community comes together to celebrate. This long-standing local tradition offers something for everyone, from live entertainment and classic small-town festivities to food, games, and evening excitement. Event Highlights […]
31 Jul - 01 Aug
All Day
Van Lear Historical Society Coal Miner's Museum
78 Millers Creek Rd, Van Lear, KY, United States, 41265
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