Upcoming Events

• Sat, Sep 26

  The Bourbon Gospel Writers Round / 

  Columbia, TN

  Buy Tickets

  Sep 26, 2026, 7:30 PM – 9:30 PM

  Columbia, TN, 807A S Garden St, Columbia, TN 38401, USA
• Fri, Oct 02

  Flint Hill *Hometown Show* / 

  Fiesta Hill Mexican Bar & Grill

  Learn more

  Oct 02, 2026, 5:00 PM – 8:30 PM

  Fiesta Hill Mexican Bar & Grill, 5074 Hwy P, Wentzville, MO 63385, USA

  Come hang with Matt at his hometown Shows Friday & Saturday in Flint Hill
• Sat, Oct 03

  Flint Hill *Hometown Show* / 

  Fiesta Hill Mexican Bar & Grill

  Learn more

  Oct 03, 2026, 5:00 PM – 8:30 PM

  Fiesta Hill Mexican Bar & Grill, 5074 Hwy P, Wentzville, MO 63385, USA

  Come hang with Matt at his hometown Shows Friday & Saturday in Flint Hill
• Sat, Oct 10

  Pensacola Beach Songwriters Festival / 

  Pensacola, FL

  Buy Tickets

  Oct 10, 2026, 5:00 PM

  Pensacola, FL, Pensacola, FL, USA

  This festival takes place over several days of incredible music! Matt Wynn will play the 10th & 11th.
• Sun, Oct 11

  Pensacola Beach Songwriters Festival / 

  Pensacola, FL

  Buy Tickets

  Oct 11, 2026, 5:00 PM

  Pensacola, FL, Pensacola, FL, USA

  This festival takes place over several days of incredible music! Matt Wynn will play the 10th & 11th.
• Fri, Oct 23

  Crusaderfest / 

  O'Fallon, MO

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  Oct 23, 2026, 6:00 PM – 8:00 PM

  O'Fallon, MO, 31 St Dominic Dr, O'Fallon, MO 63366, USA

  An evening of music and fun at Matt Wynn's High School's Alumni event!
• Sun, Oct 25

  Destin Songwriters Festival - Operation Song Round / 

  Destin, FL

  Buy Tickets

  Oct 25, 2026, 2:00 PM

  Destin, FL, Destin, FL 32541, USA
• Sat, Sep 19

  Operation Song at ESAM / 

  Empire State Aerosciences Museum

  Details

  Sep 19, 2026, 6:00 PM

  Empire State Aerosciences Museum, 250 Rudy Chase Dr, Glenville, NY 12302, USA
• Fri, Sep 18

  Operation Song Family & Sponsor Night / 

  Capital Region Veterans Memorial

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  Sep 18, 2026, 6:00 PM

  Capital Region Veterans Memorial, 338 N Ballston Ave, Schenectady, NY 12302, USA

  Private Event - closed to public
• Sat, Sep 12

  Rankin Street Fair / 

  Rankin, IL

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  Sep 12, 2026, 6:00 PM

  Rankin, IL, Rankin, IL 60960, USA
• Fri, Sep 11

  Gibson City Harvest Fest with Drew Baldridge / 

  Gibson City, IL

  Details

  Sep 11, 2026, 7:30 PM – 11:30 PM

  Gibson City, IL, Gibson City, IL 60936, USA
• Wed, Sep 09

  A Night In Uganda - Amazima Ministries / 

  The Factory at Franklin

  Details

  Sep 09, 2026, 7:00 PM

  The Factory at Franklin, 230 Franklin Rd, Franklin, TN 37064, USA
• Fri, Aug 28

  The Red Wheel Songwriters Round / 

  Franklin, TN

  Details

  Aug 28, 2026, 5:00 PM

  Franklin, TN, 230 Franklin Rd, Franklin, TN 37064, USA

  An Intimate fun evening of stories behind great songs featuring Matt Wynn, Mark Nesler & Billy Montana
• Sat, Aug 22

  Private Event / 

  Newfoundland, Canada

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  Aug 22, 2026, 7:00 PM – 11:00 PM

  Newfoundland, Canada, Newfoundland and Labrador, Canada
• Sun, Aug 16

  Private Event / 

  Nashville, TN

  Details

  Aug 16, 2026, 5:00 PM – 8:00 PM

  Nashville, TN, Nashville, TN, USA
• Thu, Aug 13

  WIXY 100.3 at Pard’s Western Shop in Urbana / 

  Pard's Western Shop

  Learn more

  Aug 13, 2026, 5:00 PM – 7:00 PM

  Pard's Western Shop, 306 N Maple St, Urbana, IL 61802, USA

  Totally Free Event!! Be in the first 100 ppl for a free show and chance to win prizes!
• Tue, Jul 28

  Shows In Alaska / 

  Alaska

  Jul 28, 2026, 7:00 PM – Aug 01, 2026, 11:00 PM

  Alaska, Alaska, USA
• Fri, Jul 17

  4th Annual Diamond Succulent Bar / 

  Murfreesboro, TN

  Details

  Jul 17, 2026, 6:00 PM – 9:00 PM

  Murfreesboro, TN, 1527 Rutledge Way, Murfreesboro, TN 37129, USA

  A fun evening experience benefiting Second Harvest Food Bank of Middle Tennessee—and celebrating Classy Cactus Farm’s 6-Year Anniversary.