• HalloWinchester Pub Crawl

    Loudoun Street Pedestrian Mall

    Winchester’s biggest Halloween street party is back! Live music, alien vibes, $500 in costume prizes + raffle gift basket — all benefiting Katie’s Comfort House.

    $10
  • HalloWinchester Old Town Merchant Trick r Treat

    Loudoun Street Pedestrian Mall

    Bring the family to Old Town Winchester for a safe and festive afternoon of trick-or-treating! Local merchants along the Loudoun Street Pedestrian Mall will be handing out candy and goodies to children in costume. Stroll through downtown, show off your Halloween spirit, and enjoy the seasonal decorations, shops, and restaurants that make Old Town such […]

    Free