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Matt Rife

Adam Sandler

Shane Gillis

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Matt Mathews

        <h2>Guide to Live Events in Winchester: Concerts, Sports and Shows Near You</h2>
<p>Winchester, Virginia, is a historic city known for its community concerts, local theater productions, college sports events, and annual festivals such as the Apple Blossom Festival.</p><p>Whether you’re cheering on a local team or seeing a touring artist nearby, Vivid Seats helps you secure tickets for every live event.</p>
        
        <h2>Things to Do in Winchester This Week</h2> 
        
<p>This week near Winchester you can lose yourself in a rap spectacular when <a href="https://www.vividseats.com/lil-wayne-tickets/performer/10268">Lil Wayne</a> takes the stage at <a href="https://www.vividseats.com/lil-wayne-tickets-bristow-jiffy-lube-live-7-30-2025--concerts-rap-hip-hop/production/5794896">Jiffy Lube Live</a> or rock out with <a href="https://www.vividseats.com/live-band-tickets/performer/470">+LIVE+ - Band</a> at the same venue. If pop nostalgia is calling belt out to <a href="https://www.vividseats.com/woah-a-90s-tribute-tickets/performer/133454">WOAH: A 90s Tribute</a> at <a href="https://www.vividseats.com/woah-a-90s-tribute-tickets-leesburg-tally-ho-8-2-2025--concerts-pop/production/5873501">Tally Ho</a> in Leesburg right on the edge of the region. Sports fans won’t want to miss the <a href="https://www.vividseats.com/frederick-keys-tickets--sports-minor-league-baseball/performer/55230">Frederick Keys</a> swinging into action at <a href="https://www.vividseats.com/frederick-keys-tickets-harry-grove-stadium-8-3-2025--sports-minor-league-baseball/production/5287059">Harry Grove Stadium</a>. And the local theater scene shines with the crowning glamour of <a href="https://www.vividseats.com/miss-miss-teen-maryland-tickets--theater-other-theater/performer/142292">Miss & Miss Teen Maryland</a> at Frederick’s <a href="https://www.vividseats.com/miss-miss-teen-maryland-tickets-frederick-weinberg-center-for-the-arts-8-2-2025--theater-other-theater/production/5874270">Weinberg Center For The Arts</a>.</p>        
        <h2>Things to Do in Winchester Next Week</h2> 
        
<p>Next week music lovers near Winchester can head to Jiffy Lube Live to catch the energetic <a href="https://www.vividseats.com/volbeat-tickets/performer/21676">Volbeat</a> on August 7 and the timeless <a href="https://www.vividseats.com/doobie-brothers-tickets/performer/251">Doobie Brothers</a> on August 9. Country and folk fans will find intimate shows by <a href="https://www.vividseats.com/the-lacs-tickets/performer/33519">The Lacs</a> in Leesburg on the 7th or <a href="https://www.vividseats.com/jamey-johnson-tickets/performer/8418">Jamey Johnson</a> at Hollywood Casino at Charles Town Races on the 9th. Comedy enthusiasts can catch the sharp wit of <a href="https://www.vividseats.com/the-washington-roast-tickets--theater-comedy/performer/161244">The Washington Roast</a> at Tally Ho, while blues aficionados can groove along with <a href="https://www.vividseats.com/shemekia-copeland-tickets/performer/8339">Shemekia Copeland</a> on August 10.</p>

Winchester VA

United States

Virginia

Concert, Comedy, Sports & Theater Tickets in Winchester, VA

Live Events near Winchester, VA

Hollywood Casino at Charles Town Races

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Matt Mathews at Hollywood Casino at Charles Town Races

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Matt Mathews Hollywood Casino at Charles Town Races in Charles Town, WV Fri, Sep 19 at 8:00pm