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  • Coastal Virginia (COVA) Kickball Tournament

    Piankatank Ruritan Club 7138 Buckley Hall Road, Mathews, VA, United States

    Get ready to PLAY BALL! It’s so easy to join in the fun- pick a Captain, add 9 others to make a 10-person team*, and get ready to compete for a trophy – and bragging rights! Each player receives a team shirt included with registration. Registration Closes April 21. *$250/ 10-member team; for larger teams, […]

    $250

  • Tour de Chesapeake

    Williams Wharf 1039 Williams Wharf Road, Mathews, VA, United States

    Premier cycling event on the beautiful Chesapeake Bay with 4 concise routes, each around 25 miles, which take cyclists from our own Gwynn's Island to Bethel Beach to the New Point Lighthouse. Each route has fully stocked rest stops, SAG support and lovely views galore! You may ride any route as many times as you […]

    $35

  • Mathews Micro Triathlon Series

    Williams Wharf 1039 Williams Wharf Road, Mathews, VA, United States

    Now in its 6th year, the Mathews Micro Triathlon Series kicks off in June for another 4-event series. Ideal for beginners to the sport of triathlon OR for experienced who want an opportunity to train & compete. MMTS #3 has options for Micro OR Sprint distances. Awards presented at the final series event in August […]

    $30

  • Islander Regatta

    Islander Hotel & Resort 633 Old Ferry Road, Mathews, VA, United States

    Annual 9 mile paddling event for non-motorized craft, circumnavigating one of Virginia’s few inhabited islands: Gwynn’s Island in Mathews County. With its origins as a fun summer challenge for a group of friends, the Islander Regatta is opening its door to more participants. Max 200.

    $65

  • CANCELED!! Wharf to Wharf Swim

    Williams Wharf 1039 Williams Wharf Road, Mathews, VA, United States

    This event has been canceled for 2023. Join us for a one mile out and back open water swim across the East River to benefit the Williams Wharf Project. There will be live music, awards, and food and drinks. Registration is at 12 PM.

  • Mathews Marathon, Half Marathon & Relay

    Put-In-Creek Landing 50 Brickbat Road, Mathews, VA, United States

    Run along peaceful, rural backroads in beautiful Mathews County, Virginia. Enjoy the fast, flat course that winds through dirt, gravel and paved roads and past the serenity of one of Virginia’s last great countrysides. Registration will close on October 5, cost will increase on Sept 1, 2023.

    $50

  • Rotary Club’s Annual Rockfish Tournament

    Mathews, VA, United States

    The Mathews Rotary Club is hosting its annual Rockfish Tournament. The entry fee is $200/ boat with unlimited anglers. Captains Registration is December 8th from 5-7 PM at Morningstar Marina. $4,000 in guaranteed cash prizes available, including a first prize of $2,000! Contact 804-725-6213 for more information.

    $200

  • Gwynn’s Island Race

    Mathews, VA, United States

    4m Run, 10m Ride or Run/Ride Duathlon: Gwynn’s Island in Mathews County is the host site of this annual race. Join runners & riders in this unique tour of one of Virginia’s special locations – then hang around to enjoy the music & food. 4 mile road run Starting and ending at the Gwynn’s Island […]

  • 25th Annual Tour de Chesapeake

    Williams Wharf 1039 Williams Wharf Road, Mathews, VA, United States

    Located in Mathews, VA, on the beautiful Chesapeake Bay, the Tour de Chesapeake cycling event, now in its 25th year, offers rural, flat roads that all lead to water. There are 4 concise routes, each around 25 miles, which take cyclists from our own Gwynn's Island to Bethel Beach to the New Point Lighthouse.  Each […]

    $35

  • MHS Athletics Presents… Comedy Night!

    Harry M. Ward Auditorium at Mathews High School 9889 Buckley Hall Road, Mathews , VA, United States

    Join the Mathews High School Athletics Department for Comedy Night, featuring Tom Holaday, Sonya King and Sid Bridge! Tickets are $15 in advance, or $20 at the door, and can be purchased at MHS, Howard-Dooley Care, Mathews Pharmacy and Morgan & Edwards Real Estate.

    $20

  • Saltwater Learn to Fish Day

    Williams Wharf Landing 1039 Williams Wharf Road, Mathews, VA, United States

    Fishing & Learning Stations, children will be required to wear life jackets while fishing.  Participants will be asked to sign a waiver.  Refreshments provided!  Rain or Shine (the fish don’t care)! 

  • Family Port Fun Day!

    Port Fun Park 9763 Buckley Hall Road, Mathews, VA, United States

    Join Mathews Parks & Facilities for a Family Fun Day at Port Fun Park! There will be activities on the new basketball courts, lessons and play time on the pickleball courts, an adult fitness trail, playground activities and the Mathews Memorial Library's Trail Tales! There will also be vendor giveaways and snow cones from Pelican's […]

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