• Patsy Cline Block Party

    Celebrate one Winchester’s most famous natives, country music singer, Patsy Cline at this old-fashioned block party with live entertainment, food, and souvenirs in front of the Patsy Cline Historic House. Labor Day Weekend.

  • Richard’s Fruit Market Apple Festival

    This free festival celebrates the apple harvest. Featuring live music, hay wagon rides, farm animal petting zoo, yard games, farm food, a tasting table, wine and craft beer, and of course, LOTS of apples! Mid-October.

  • Richard’s Fruit Market Peach Festival

    This free festival celebrates the arrival of peaches! Enjoy peach pies, peach milkshakes, and fresh peaches galore. Live music, hay wagon rides, petting zoo, yard games, farm food, and wine and beer tasting. Mid-August.

  • Rockin’ Independence Eve

    This annual All-American celebration includes live music, street performers, kids’ activities, and a spectacular fireworks show in Old Town Winchester. July 3.

  • Route 11 Yard Crawl

    The Route 11 Yard Crawl is over 43 miles of yard sales and business sales, from Stephens City to New Market. It’s Virginia’s largest yard sale, offering hundreds of individual yard sales, shopping and food trucks.

  • Shenandoah Apple Blossom Festival

    A family-friendly festival that includes more than 30 events: band competitions, dances, a Firefighter’s Parade, a Grand Feature Parade, a 10K race, a carnival, celebrities, Weekend in the Park, and much more! Late April – Early May.

    Apple Blossom Festival
  • Shenandoah Valley Apple Harvest Festival

    Held annually for over 40 years, this festival celebrates apples! Arts and crafts show, live music, apple pie eating contest, apple butter making, bingo, inflatables, face painting, and craft beer and hard cider tastings. Third Weekend in September.

  • Skyline Indie Film Fest

    An independent film festival bringing the best in new, undistributed indie film from around the corner and around the world to Old Town Winchester! Held in September.

  • St. Paddy’s Celtic Fest

    This free festival celebrates the community’s Irish and Scottish heritage with Celtic inspired music, dance, and the City of Winchester Pipes and Drums performing in Old Town businesses and along the Loudoun Street Mall. Second weekend in March.

  • Winchester Greek Festival

    Sample legendary Greek cuisine and experience Greek music and dance at this free festival. A kids zone makes this great fun for the entire family! Mid-August.