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  • Mathews Paint Out

    Bay School Community Arts Center 279 Main Street , Mathews, VA, United States

    For the fourth year, the Plein Air Invitational is partnering with the Mathews County Bay School Community Arts Center for a one-day event in Mathews. The 2026 Plein Air Artists […]

  • Oyster Seed Hatchery Tours & Tastings

    Oyster Seed Holdings 425 Callis Wharf Rd, Grimstead, VA, United States

    Every other Friday from May through June, visitors can experience a tour and tasting experience at Oyster Seed Holdings to see how farm-raised oysters get their start. Guests will start […]

    $25

  • Tall Ship Godspeed

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

    Tall Ship Godspeed Public Afternoon Tours at Williams Wharf Step aboard history this summer as the Tall Ship Godspeed visits Williams Wharf for special public afternoon tours. A replica of […]

    Free

  • Juneteenth Freedom Day

    Cobbs Creek Arts Center 61 Cobbs Creek Lane, Cobbs Creek, VA, United States

    Join us as we honor freedom, culture, and community.  There will be delicious food trucks, unique local vendors, a full lineup of entertainment, music performances, and family-friendly fun.  Bring your […]

    Free

  • Oyster Seed Hatchery Tours & Tastings

    Oyster Seed Holdings 425 Callis Wharf Rd, Grimstead, VA, United States

    Every other Friday from May through June, visitors can experience a tour and tasting experience at Oyster Seed Holdings to see how farm-raised oysters get their start. Guests will start […]

    $25

  • 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

  • Gwynn’s Island Festival

    Gwynn's Island Festival 1996 Old Ferry Road, Gwynn, VA, United States

    Gwynn’s Island Festival Saturday, June 27th Last Saturday in June, 9am to 4pm. Gwynn’s Island FestivalCelebrating the History and Culture of Gwynn’s Island Join the community for the annual Gwynn’s […]

    Free

  • Crickets on a Hill

    Harry M. Ward Auditorium - Mathews High School 9889 Buckley Hall Rd, Mathews, VA, United States

    A Revolutionary Musical Returns to the Stage Experience local history brought to life through music, drama, and community theater as Crickets on a Hill returns to the stage in celebration […]

    $5 – $10

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