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Kenny Wayne Shepherd

<h2>Guide to Live Events in Winchester: Concerts, Sports and Shows Near You</h2>
<p>Winchester, VA offers a lively mix of local concerts, theater performances, and community festivals throughout the year. From intimate venues to campus and civic events, there’s always something happening in the area.</p><p>When you’re ready to go, Vivid Seats makes it easy to find and purchase tickets for events in and around Winchester.</p>
        
        <h2>Things to Do in Winchester This Week</h2> 
        
<p>Make your week around Winchester buzz with big shows nearby: <a href="https://www.vividseats.com/randy-travis-tickets/performer/708">Randy Travis</a> at The Maryland Theatre in Hagerstown on Thursday, then stand-up star <a href="https://www.vividseats.com/josh-johnson-tickets--theater-comedy/performer/67955">Josh Johnson</a> bringing laughs to Hollywood Casino at Charles Town Races on Friday. Rock fans can catch <a href="https://www.vividseats.com/bruce-in-the-usa-tickets/performer/113792">Bruce in the USA - Bruce Springsteen Tribute</a> at Weinberg Center For The Arts in Frederick the same night, or keep the hits rolling with <a href="https://www.vividseats.com/38-special-tickets/performer/4471">38 Special</a> back at Hollywood Casino at Charles Town Races on Saturday. If you crave heavier sounds, <a href="https://www.vividseats.com/revocation-tickets/performer/43666">Revocation</a> storms Leesburg's Tally Ho on Thursday and <a href="https://www.vividseats.com/mushroomhead-tickets/performer/5377">Mushroomhead</a> caps the weekend there on Sunday.</p>        
        <h2>Things to Do in Winchester Next Week</h2> 
        
<p>Next week around Winchester, catch <a href="https://www.vividseats.com/priscilla-presley-tickets--theater-public-speaking/performer/49697">Priscilla Presley</a> at Weinberg Center For The Arts in nearby Frederick on October 22. Then rock out in Leesburg with <a href="https://www.vividseats.com/new-potato-caboose-tickets/performer/30211">New Potato Caboose</a> at Tally Ho on October 24, followed by <a href="https://www.vividseats.com/the-rush-experience---rush-tribute-tickets/performer/153885">The Rush Experience - Rush Tribute</a> at the same club the next night. Classical fans can head to Manassas for <a href="https://www.vividseats.com/manassas-symphony-orchestra-tickets/performer/64800">Manassas Symphony Orchestra</a> on October 25 and <a href="https://www.vividseats.com/time-for-three-tickets/performer/17060">Time for Three</a> on October 26 at Hylton Performing Arts Center - Merchant Hall. For a festive change of pace, take in the <a href="https://www.vividseats.com/mummers-day-parade-tickets--theater-arts-and-theater/performer/148602">Mummers Day Parade</a> at The Maryland Theatre in Hagerstown on October 25.</p>

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Hollywood Casino at Charles Town Races

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Kenny Wayne Shepherd at Hollywood Casino at Charles Town Races

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Kenny Wayne Shepherd Hollywood Casino at Charles Town Races in Charles Town, WV Sat, Apr 18, 2026 at 8:00pm