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  • 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.

  • Rehoboth Beach Jazz Festival

    Rehoboth Beach Convention Center & various local venues, DE Rehoboth Beach Convention Center & various local venues, DE

    World-class smooth jazz, gospel, and R&B across coastal venues.

  • Annual Chili-Chowder Cookoff

    Chincoteague, VA Chincoteague, VA

    Local fall classic to sample the shore's best clam chowders, seafood dishes, and chilis.

  • Blackbird Creek Fall Festival

    Blackbird Creek Reserve, 801 Blackbird Landing Road, Townsend, DE Blackbird Creek Reserve, 801 Blackbird Landing Road, Townsend, DE

    Free family-fun day celebrating natural beauty of the reserve.

    Free

  • Parktober Fest

    Delaware Park Casino, Wilmington, DE Delaware Park Casino, Wilmington, DE

    Fall festival celebration with food, drinks, and entertainment.

  • Eyreville Open House

    Historic Eyreville, 3259 Eyreville Drive, Cape Charles, VA Historic Eyreville, 3259 Eyreville Drive, Cape Charles, VA

    Explore historic grounds with archaeologist presentation, hors d'oeuvres, and drinks.

  • The Halloween Ghost Ship

    Kalmar Nyckel Foundation Shipyard, Historic New Castle, DE Kalmar Nyckel Foundation Shipyard, Historic New Castle, DE

    9th annual spooky maritime celebration with shipyard atmosphere for all ages.

  • Autumn at Asbury: A Fall Festival

    Asbury United Methodist Church, 1401 Camden Avenue, Salisbury, MD Asbury United Methodist Church, 1401 Camden Avenue, Salisbury, MD

    Outdoor neighborhood bash with inflatable obstacle course, silent auction, and Trunk or Treat.

  • Souper Saturday: Minestrone

    Island Community House, 6246 Mumford Street, Chincoteague, VA Island Community House, 6246 Mumford Street, Chincoteague, VA

    Community lunch featuring homemade minestrone soup, garlic bread, and drinks.

    $12