Annual Events

Annual Events

  • Battlefield Half Marathon

    Experience all the beauty of fall in the Shenandoah Valley running in the area’s premier half marathon and relay. The starting line is located in historic Kernstown Battlefield with the majority of the course following scenic country roads. November.

  • Bloomin’ Wine Fest

    Enjoy live entertainment on several stages, festival food, artisan displays, Virginia wines, craft beer, and wonderful company in historic Old Town Winchester. This event is the kick-off for the Shenandoah Apple Blossom Festival. Late April.

    • 1 N. Loudoun Street
      Winchester, VA 22601
    • (540) 662-3863
    • thebloom.com

  • Candlelight and Holiday Tours

    Tour Belle Grove Plantation’s historic Manor House during the holidays, where area Garden Clubs adorn each room with natural decorations. Enjoy festive live music and holiday treats. End of November-December.

    • 336 Belle Grove Road
      Middletown, VA 22645
    • (540) 869-2028
    • bellegrove.org

  • Celebración

    This family-oriented free festival celebrates Hispanic Heritage Month with dance performances, children’s activities, live music, delicious food, and cultural vendors. Mid-September.

  • Civil War Weekend

    Numerous Civil War sites in the area host special programs, tours, and more. Third weekend of August.

  • First Night Winchester

    This celebration of the arts brings performers to numerous venues in Old Town Winchester, ending with a countdown, fireworks, and an “apple drop” to ring in the New Year. December 31.

    First Night Winchester

  • Fourth of July Celebration at Sherando Park

    Frederick County’s Independence Day celebration is held at Sherando Park and includes a day of swimming at the outdoor pool, live music, and plenty of room to spread out your blankets to enjoy the fireworks show. July 4.

  • Frederick County Fair

    Livestock, petting zoo, pageants, demolition derby, tractor pulls, monster trucks, educational exhibits, a carnival, live music, and traditional fair food are just some of the reasons to come to the fair! Last week of July.

  • Garden Fest at Belle Grove Plantation

    Garden Fest is a plant sale hosted by the Northern Shenandoah Valley Master Gardener Association and includes hands-on workshops, garden and specialty vendors, children’s activities, tours of the historic Manor House, and more. Early June.

    • 336 Belle Grove Road
      Winchester, VA 22645
    • (540) 869-2028
    • bellegrove.org
    garden fest belle grove

  • Holiday House Tours

    Tour a variety of local and historic homes beautifully decorated for the holiday season at this long-running Winchester event that began in 1975, and is hosted by Preservation of Historic Winchester. Early December.

    • 530 Amherst Street
      Winchester, VA 22601
    • (540) 667-3577
    • www.phwi.org