Annual Events

Annual Events

  • Holly Jolly Old Town Celebration

    Get in the holiday spirit with caroling from local choral groups, horse-drawn wagon rides, and specials at shops and restaurants. Children can make a craft and meet Santa for photos at Santa’s Headquarters. Early December.

  • Hop Blossom Craft Beer Festival

    Beer festival featuring 40+ breweries, a homebrew competition, and live music in Old Town Winchester. Mid-June.

    Hop Blossom Beer Festival

  • Kidz Fest

    This free, family-friendly event features over 50 interactive exhibits highlighting education, art, music, sports and more. Petting zoo, games, and live performances take place along the Loudoun Street Mall.

  • Middletown Christmas Parade

    This small, hometown parade features horses, floats, bands and more leading the way for Santa and Mrs. Claus to travel down Main Street. Early December.

  • Middletown’s 4th of July Celebration and Parade

    The small town of Middletown hosts this all-day event featuring a softball tournament, food and craft vendors, inflatables for the kids, a parade down Main Street, and live music in the town park before an awesome fireworks show. July 4.

  • N-SSA Spring and Fall Competitions

    The N-SSA is the country’s oldest and largest Civil War shooting sports organization. Member units compete in live-fire matches with original or authentic reproduction Civil War period muskets, rifles, revolvers, mortars and cannons. May and October.

  • Newtown Heritage Festival

    A free family festival that celebrates the town of Stephens City’s heritage and includes wagon rides, a parade, a craft show, and fireworks. May – Memorial Day Weekend.

    Newtown Heritage Festival

  • Of Ale and History Beer Festival

    Sample an array of beers from the New and Old World. Music provided by live bands, food, and tours of the historic home, all in a scenic outdoor setting. May – Mother’s Day Weekend.

    • 336 Belle Grove Road
      Middletown, VA 22645
    • (540) 869-2028
    • bellegrove.org
    Of Ale and History Beer Festival

  • Oktoberfest

    Taste German-inspired food, beers, and global wine while also experiencing different parts of German culture. Costumed professional Bavarian dancers, traditional German and German inspired music, street performers, and more. October.

  • Old Town Winchester Christmas Parade

    Bands, floats, and specialty units along with Santa parade through Old Town Winchester, followed by the lighting of the huge Christmas tree on the Loudoun Street Mall. Held the Monday after Thanksgiving.

    • Piccadilly Street at Cameron to Braddock to Cork at Loudoun
      Winchester, VA 22601
    • (540) 662-4946
    • oldtownwinchesterva.com