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  • Pumpkin Patch Sundays at Loblolly Acres

    3893 Turkey Point Road, Viola, DE 19979 3893 Turkey Point Road, Viola, DE 19979

    Small-town pumpkin picking and crisp autumn air.

  • Ocean View Shell-ebration: Oyster Week

    Ocean View Brewing Company, Ocean View, DE Ocean View Brewing Company, Ocean View, DE

    Week-long celebration pairing fresh local oysters with cold craft brews.

  • Greyhounds Reach the Beach

    Rehoboth Beach Convention Center, 229 Rehoboth Avenue, Rehoboth Beach, DE Rehoboth Beach Convention Center, 229 Rehoboth Avenue, Rehoboth Beach, DE

    Heartwarming annual gathering for greyhound and sighthound adopters.

  • VA250 Mobile Museum Experience

    Historic Ker Place, 69 Market Street, Onancock, VA Historic Ker Place, 69 Market Street, Onancock, VA

    Free traveling educational exhibition highlighting Virginia's role in the American Revolution.

    Free

  • Sea & Soul Retreat

    Nature-immersive wellness retreat focusing on personal growth and peaceful coastal surroundings.

  • Fifth Annual Crisfield Heritage Festival

    Crisfield Heritage Foundation, 3 9th Street, Crisfield, MD Crisfield Heritage Foundation, 3 9th Street, Crisfield, MD

    Authentic Chesapeake Bay culture celebrating lower shore identity.

  • Cape Charles Fall Festival

    Mason Avenue, Strawberry Street, and Strawberry Plaza, Cape Charles, VA Mason Avenue, Strawberry Street, and Strawberry Plaza, Cape Charles, VA

    Massive local celebration with classic parade, white boot auction, artisans, and scarecrow contest.

  • Bethany UMC Wild West Block Party

    Bethany United Methodist Church, 8648 Stephen Decatur Highway, Berlin, MD Bethany United Methodist Church, 8648 Stephen Decatur Highway, Berlin, MD

    Free community festival featuring bounce houses, games, live music, and snacks.

    Free

  • ESO FEST 2026

    ESO Arts Center, 15293 King Street, Belle Haven, VA ESO Arts Center, 15293 King Street, Belle Haven, VA

    Multi-disciplinary arts festival with local artists, performances, and vendor market.

    $17

  • Pink Power Hoedown 2026

    American Legion Post 17, Green Hill, MD American Legion Post 17, Green Hill, MD

    Community fundraiser and hoedown event.

  • St. Charles Oktoberfest

    St. Charles Catholic Church, 549 Randolph Avenue, Cape Charles, VA St. Charles Catholic Church, 549 Randolph Avenue, Cape Charles, VA

    Family-friendly parish event with authentic German food, music, beer, and games.