2026 Fiddles and Fifths Bluegrass and Bourbon Festival - Saturday (9/12)

Fiddles and Fifths Bluegrass and Bourbon Festival

<h2>Guide to Live Events in Winchester: Concerts, Sports and Shows Near You</h2>
<p>Winchester, VA, is a lively center for local events, offering everything from concerts and theater performances to music festivals. Whether you're eager to see a favorite artist live or enjoy a thrilling show, Vivid Seats has you covered.</p>
        
<h2>Things to Do in Winchester This Week</h2> 
        
<p>This week in Winchester, VA, offers a vibrant mix of entertainment to suit all interests. Catch the electrifying <a href="https://www.vividseats.com/pitbull-tickets/performer/6663">Pitbull</a> concert at <a href="https://www.vividseats.com/pitbull-tickets-bristow-jiffy-lube-live-8-19-2026--concerts-rap-hip-hop/production/6529707">Jiffy Lube Live</a> in Bristow for a night filled with energy. If nostalgic tunes are your thing, <a href="https://www.vividseats.com/so-fetch-2000s-tribute-band-tickets/performer/75606">So Fetch - 2000s Tribute Band</a> and <a href="https://www.vividseats.com/nirvani---nirvana-tribute-tickets/performer/153864">Nirvani - Nirvana Tribute</a> will both grace the stage at <a href="https://www.vividseats.com/nirvani---nirvana-tribute-tickets-leesburg-tally-ho-8-21-2026/production/6957418">Tally Ho</a> in Leesburg on consecutive nights.</p>
<p>For those intrigued by the theatrical, the <a href="https://www.vividseats.com/serial-killer-speakeasy-tickets--theater-other-theater/performer/526284">Serial Killer Speakeasy</a> at <a href="https://www.vividseats.com/serial-killer-speakeasy-tickets-hagerstown-the-maryland-theatre-8-22-2026/production/7276316">The Maryland Theatre</a> in Hagerstown promises a unique show. Sports enthusiasts can cheer on <a href="https://www.vividseats.com/loudoun-united-fc-tickets--sports-soccer/performer/99070">Loudoun United FC</a> at <a href="https://www.vividseats.com/loudoun-united-fc-tickets-leesburg-segra-field-8-22-2026/production/6431794">Segra Field</a> or catch a game with the <a href="https://www.vividseats.com/hagerstown-flying-boxcars-tickets--sports-minor-league-baseball/performer/174241">Hagerstown Flying Boxcars</a> at <a href="https://www.vividseats.com/hagerstown-flying-boxcars-tickets-meritus-park-8-23-2026--sports-minor-league-baseball/production/6000009">Meritus Park</a>. Each event promises a memorable experience, making it a week not to miss!</p>
        
        

<h2>Things to Do in Winchester Next Week</h2> 
        
<p>Next week in Winchester, VA, music enthusiasts can look forward to an intimate performance by <a href="https://www.vividseats.com/noah-guthrie-tickets/performer/43939">Noah Guthrie</a> at the <a href="https://www.vividseats.com/noah-guthrie-tickets-winchester-bright-box-theater-8-30-2026/production/7416075">Bright Box Theater</a> on August 30. If you're up for a little drive, <a href="https://www.vividseats.com/crowder-tickets/performer/9918">Crowder</a> will deliver soulful tunes at the <a href="https://www.vividseats.com/crowder-tickets-woodstock-shenandoah-downs---county-fair-association-8-28-2026/production/6641399">Shenandoah Downs - County Fair Association</a> in Woodstock on August 28.</p><p>Rock out to <a href="https://www.vividseats.com/that-arena-rock-show-tickets/performer/98961">That Arena Rock Show</a> at <a href="https://www.vividseats.com/that-arena-rock-show-tickets-leesburg-tally-ho-8-29-2026/production/7187613">Tally Ho</a> in Leesburg on August 29. For something a bit different, check out the thrilling <a href="https://www.vividseats.com/truck-and-tractor-pull-tickets--sports-motorsports/performer/18420">Truck and Tractor Pull</a> back at Shenandoah Downs on August 30. Whether you're into live concerts or live engines, this week offers excitement for all tastes.</p>

<h2>Upcoming Concerts in Winchester: Live Music & Tour Dates Near You</h2>

<p>Winchester is a vibrant city for live music, hosting a variety of artists on stages of all sizes. From arena tours to club shows, there's always a concert to enjoy in Winchester, and Vivid Seats is here to help you find your next unforgettable night out.</p>

<h2>Frequently Asked Questions about Winchester Concert Tickets</h2>

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<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What are some upcoming concerts in Winchester this week?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
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        <p>
If you're in Winchester this week, check out nearby concerts: Pitbull at Jiffy Lube Live in Bristow on August 19; Nirvani, a Nirvana tribute, at Tally Ho in Leesburg on August 21; and So Fetch, a 2000s tribute band, at Tally Ho in Leesburg on August 22. These shows cover rap/hip hop, rock, and pop across two lively venues. Pick a night and enjoy live music.
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<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What are some upcoming concerts in Winchester next week?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
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      <p>
      

Next week in and around Winchester catch <a href="https://www.vividseats.com/crowder-tickets/performer/9918">Crowder</a> at <a href="https://www.vividseats.com/crowder-tickets-woodstock-shenandoah-downs---county-fair-association-8-28-2026/production/6641399">Shenandoah Downs - County Fair Association</a>, <a href="https://www.vividseats.com/that-arena-rock-show-tickets/performer/98961">That Arena Rock Show</a> at <a href="https://www.vividseats.com/that-arena-rock-show-tickets-leesburg-tally-ho-8-29-2026/production/7187613">Tally Ho</a>, and <a href="https://www.vividseats.com/noah-guthrie-tickets/performer/43939">Noah Guthrie</a> at <a href="https://www.vividseats.com/noah-guthrie-tickets-winchester-bright-box-theater-8-30-2026/production/7416075">Bright Box Theater</a>.

From a county fair stage to intimate theater rooms, these shows offer a great mix of sounds for music fans in the Winchester area next week.

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<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">How can I find upcoming concerts in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <p itemprop="text">Finding upcoming concerts in Winchester is easy on Vivid Seats. At the top of this page, you’ll find a search and discovery tool highlighting the most popular concerts and upcoming events in the city. You can browse by artist, venue, genre, or date to explore shows happening this week and beyond, all with real-time ticket availability and seating options.</p>
    </div>
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  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Can I get last-minute concert tickets in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Yes, you can often find last-minute concert tickets in Winchester on Vivid Seats. Whether you’re planning ahead or making a spontaneous decision, Vivid Seats makes it easy to secure verified tickets right up until showtime.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Is Vivid Seats legit for concert tickets in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <p itemprop="text">Yes! Vivid Seats is a trusted ticket marketplace used by over 100 million fans. When you buy Winchester concert tickets on Vivid Seats, every order is backed by our 100% Buyer Guarantee. That means your purchase is safe, your tickets will arrive before the event, and they'll be valid or your money back.</p>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Are tickets guaranteed on Vivid Seats?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Absolutely. Every Winchester concert ticket sold on Vivid Seats comes with our 100% Buyer Guarantee, which ensures:</p>
        <ul>
          <li>Your transaction will be secure.</li>
          <li>Your tickets will be delivered before your event.</li>
          <li>Your tickets will be valid and authentic or your money back.</li>
        </ul>
        <p>Our mission is to make buying concert tickets stress-free, so you can focus on enjoying your event.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Are fees included in the price I see on Vivid Seats?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Vivid Seats uses All-In Pricing, so you'll see the full cost of a concert ticket in Winchester, including fees, upfront as you shop. No surprises at checkout.</p>
      </div>
    </div>
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  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What happens if my Winchester concert is canceled or postponed?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>If your event is canceled, you'll receive a full refund. If an event has been postponed or rescheduled, rest assured that your tickets will be valid for the rescheduled date. For some rescheduled events, the primary source of the tickets will reissue all previously purchased tickets with new bar codes. If this occurs, the seller will notify us, and we will deliver new tickets to you and remind you to discard your old tickets.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Does Vivid Seats have a rewards program?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Yes! Vivid Seats offers a leading ticket loyalty program: Vivid Seats Rewards. Fans earn credit on every purchase, which can be redeemed for future tickets. The more events you attend, the more perks you can unlock:</p>
        <ul>
          <li>A free 11th ticket after 10 purchases</li>
          <li>Birthday rewards</li>
          <li>Seat upgrades and VIP parties</li>
          <li>Exclusive experiences like on-ice or on-field passes to your favorite team</li>
        </ul>
      </div>
    </div>
  </div>

</div>

<h2>Upcoming Sports in Winchester: Games, Teams & Matchups Near You</h2>

<p>Live sports thrive in Winchester, where fans pack venues across town all season long. From sold-out rivalry games to weekday matchups, the city’s sports venues deliver big moments for every kind of fan. Browse schedules by sport, date, or venue to find the perfect game to attend near you. Whether it’s a marquee showdown or a spontaneous night out, you can find seats on Vivid Seats.</p>

<h2>Frequently Asked Questions about Winchester Sports Tickets</h2>

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<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What sporting events are happening in Winchester this week?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
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      <p>

This week’s top sporting events include Loudoun United FC (Soccer) at Segra Field in Leesburg on August 22. Also on August 23, the Hagerstown Flying Boxcars (Minor League Baseball) play at Meritus Park in Hagerstown, MD. Both are great options for fans looking for live soccer and minor-league baseball this week.

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<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What sporting events are happening in Winchester next week?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
      <p>

Next week near Winchester, catch the <a href="https://www.vividseats.com/frederick-keys-tickets--sports-minor-league-baseball/performer/55230">Frederick Keys</a> as they take on rival clubs at <a href="https://www.vividseats.com/frederick-keys-tickets-harry-grove-stadium-8-30-2026--sports-minor-league-baseball/production/6323278">Harry Grove Stadium</a> in Frederick, MD. Also in the region, the <a href="https://www.vividseats.com/truck-and-tractor-pull-tickets--sports-motorsports/performer/18420">Truck and Tractor Pull</a> at <a href="https://www.vividseats.com/truck-and-tractor-pull-tickets-woodstock-shenandoah-downs---county-fair-association-8-30-2026/production/6641558">Shenandoah Downs - County Fair Association</a> in Woodstock, VA pits powerful machines and their crews head-to-head in a classic fairground showdown.

        </p>
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<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">How can I find upcoming games and sports events in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">Finding upcoming sports events in Winchester is easy on Vivid Seats. At the top of this page, you’ll find a discovery tool featuring the most popular teams, matchups, and games across every league. You can browse by sport, venue, or date to explore events happening this week and beyond, all with real-time ticket availability and seating options.</div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Can I get last-minute sports tickets in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Yes, you can often find last-minute sports tickets in Winchester on Vivid Seats. Whether you're planning ahead or deciding to catch a game on the fly, Vivid Seats updates listings in real time, so fans can secure verified tickets right up until kickoff, first pitch, or tipoff.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Is Vivid Seats legit for sports tickets in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <p itemprop="text">Yes! Vivid Seats is a trusted ticket marketplace used by over 100 million fans. When you buy Winchester sports tickets on Vivid Seats, every order is backed by our 100% Buyer Guarantee. That means your purchase is safe, your tickets will arrive before the event, and they'll be valid or your money back.</p>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Are sports tickets guaranteed on Vivid Seats?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Absolutely. Every Winchester sports ticket sold on Vivid Seats comes with our 100% Buyer Guarantee, which ensures:</p>
        <ul>
          <li>Your transaction will be secure.</li>
          <li>Your tickets will be delivered before your event.</li>
          <li>Your tickets will be valid and authentic or your money back.</li>
        </ul>
        <p>Our mission is to make buying sports tickets stress-free, so you can focus on enjoying the game.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Are fees included in the price I see on Vivid Seats?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Vivid Seats uses All-In Pricing, so you'll see the full cost of a sports ticket in Winchester, including fees, upfront as you shop. No surprises at checkout.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What happens if my Winchester game is canceled or postponed?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>If your game is canceled, you'll receive a full refund. If an event has been postponed or rescheduled, rest assured that your tickets will be valid for the new date. For some rescheduled games, the primary source of the tickets will reissue all previously purchased tickets with new bar codes. If this occurs, the seller will notify us, and we’ll deliver new tickets and remind you to discard your old ones.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Does Vivid Seats have a rewards program?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Yes! Vivid Seats offers a leading ticket loyalty program: Vivid Seats Rewards. Fans earn credit on every purchase, which can be redeemed for future tickets. The more events you attend, the more perks you can unlock:</p>
        <ul>
          <li>A free 11th ticket after 10 purchases</li>
          <li>Birthday rewards</li>
          <li>Seat upgrades and VIP experiences</li>
          <li>Exclusive access to pregame or on-field events with select teams</li>
        </ul>
      </div>
    </div>
  </div>

</div>

<h2>Upcoming Theater & Comedy Shows in Winchester: Plays, Musicals & Stand-Up Near You</h2>

<p>Winchester offers a variety of live entertainment, including plays and stand-up comedy. From theaters and comedy clubs to intimate performance spaces, there’s always a show to see, and Vivid Seats makes it easy to find tickets for every laugh and standing ovation.</p>

<h2>Frequently Asked Questions about Winchester Theater & Comedy Tickets</h2>

<div itemscope itemtype="https://schema.org/FAQPage">

<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What theater or comedy shows are happening in Winchester this week?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
      <p>

No theater or comedy shows are listed for Winchester, VA, in the provided event data. The only event is Serial Killer Speakeasy, an Other Theater production at The Maryland Theatre in Hagerstown on August 22 at 8:00 PM. The Maryland Theatre has a listed capacity of 1,300 for this show.

        </p>
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<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What theater or comedy shows are happening in Winchester next week?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
       <p>

Next week the standout theater pick for the Winchester area is <a href="https://www.vividseats.com/off-campus-rave-tickets--theater-other-theater/performer/539182">Off Campus Rave</a> at <a href="https://www.vividseats.com/off-campus-rave-tickets-leesburg-tally-ho-7-25-2026/production/7153752">Tally Ho</a> in nearby Leesburg on August 28, 2026 at 8:00 PM.

The show takes place at the intimate 600-seat venue and promises an energetic, offbeat night for theater and comedy fans.

        </p>
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<div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">How can I find upcoming theater and comedy shows in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <p itemprop="text">Finding upcoming theater and comedy events in Winchester is simple with Vivid Seats. At the top of this page, you'll find a carousel of popular plays, musicals, and comedy shows in the city. Browse by theater and comedy tickets in Winchester under $100, top picks, family-friendly events, venue or date to discover events happening this week and beyond, with real-time ticket availability and seating options.</p>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Can I get last-minute theater or comedy tickets in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Yes, you can often find last-minute theater and comedy tickets in Winchester on Vivid Seats. Whether it’s a spontaneous night out or a sold-out show you don’t want to miss, Vivid Seats makes it easy to secure verified tickets right up until showtime.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Is Vivid Seats legit for theater and comedy tickets in Winchester?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <p itemprop="text">Yes! Vivid Seats is a trusted ticket marketplace used by over 100 million fans. When you buy Winchester theater or comedy tickets on Vivid Seats, every order is backed by our 100% Buyer Guarantee. That means your purchase is safe, your tickets will arrive before the event, and they'll be valid or your money back.</p>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Are tickets guaranteed on Vivid Seats?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Absolutely. Every Winchester theater and comedy ticket sold on Vivid Seats comes with our 100% Buyer Guarantee, which ensures:</p>
        <ul>
          <li>Your transaction will be secure.</li>
          <li>Your tickets will be delivered before your event.</li>
          <li>Your tickets will be valid and authentic or your money back.</li>
        </ul>
        <p>Our mission is to make buying tickets stress-free, so you can focus on enjoying the show.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Are fees included in the price I see on Vivid Seats?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Vivid Seats uses All-In Pricing, so you'll see the full cost of a theater or comedy ticket in Winchester, including fees, upfront as you shop. No surprises at checkout.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">What happens if my Winchester show is canceled or postponed?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>If your show is canceled, you'll receive a full refund. If an event has been postponed or rescheduled, your tickets will remain valid for the new date. For some rescheduled performances, the primary ticket source may reissue tickets with updated barcodes. If this occurs, we’ll deliver your new tickets and remind you to discard any previous versions.</p>
      </div>
    </div>
  </div>

  <div itemprop="mainEntity" itemscope itemtype="https://schema.org/Question">
    <h3 itemprop="name">Does Vivid Seats have a rewards program?</h3>
    <div itemprop="acceptedAnswer" itemscope itemtype="https://schema.org/Answer">
      <div itemprop="text">
        <p>Yes! Vivid Seats offers a leading ticket loyalty program: Vivid Seats Rewards. Fans earn credit on every purchase, which can be redeemed for future tickets. The more events you attend, the more perks you can unlock:</p>
        <ul>
          <li>A free 11th ticket after 10 purchases</li>
          <li>Birthday rewards</li>
          <li>Seat upgrades and VIP experiences</li>
          <li>Exclusive access to special events and meet-and-greets</li>
        </ul>
      </div>
    </div>
  </div>

</div>

Winchester VA

United States

Virginia

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

Live Events near Winchester, VA

Bright Box Theater

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Fiddles and Fifths Bluegrass and Bourbon Festival at Bright Box Theater

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2026 Fiddles and Fifths Bluegrass and Bourbon Festival - Saturday (9/12) Bright Box Theater in Winchester, VA Sat, Sep 12 at 1:00pm