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  • 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 […]

  • 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 […]

    $65

  • Mathews Marathon, Half Marathon, and 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 […]

    $60

  • Christmas Comes to Gwynn’s Island

    Gwynn's Island Museum State Rte 633, Gwynn, VA, United States

    Join us on Gwynn’s Island to kick-off your Holiday Season! During this free event, see the educational exhibits that portray our rich history. As the oldest museum in Mathews County, […]

  • Gavin Dustin 5k

    Mathews Elementary School 347 Church Street, Mathews, VA, United States

    Join MHS student Gavin Dustin on the morning of April 19th as he hosts a 5k race at Mathews Elementary School to benefit the youth soccer program at the Mathews […]

    $10

  • Get Your Glow On

    Mathews, VA, United States

    Join the Mathews Little League for a Sponsorship Appreciation Night at the ball field! Let's light it up for the sponsors and everyone who makes the league possible with a […]

  • 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. Registration cost is $65 per person not per boat. Tandem kayaks, 8-person racing shells, paddle boats and even dragon boats (!!) are permitted as long as they are human powered, non-motorized. Each paddler must register […]

    $65

  • Wharf to Wharf Swim

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

    The one-mile swim will begin at 10 am in waves, based on the following categories: PUFFERFISH uses swim aids/ swim fins/ flotation device. You’re not a strong swimmer OR just want to relax in the water and will feel much more comfortable completing the one-mile distance if you use a swim aid, such as fins, a […]

    $50

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