Annual Events
Annual Events
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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.
- 6410 Middle Road
Winchester, VA 22601 - (540) 869-1455
- richardsfruitmarket.com
- 6410 Middle Road
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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.
- 6410 Middle Road
Middletown, VA 22645 - (540) 869-1455
- richardsfruitmarket.com
- 6410 Middle Road
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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.
- 1 N. Loudoun Street
Winchester, VA 22601 - 5405353660
- oldtownwinchesterva.com
- 1 N. Loudoun Street
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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.
- Route 11
Stephens City, VA 22655 - (540) 459-2542
- www.facebook.com/pg/OfficialRoute11YardCrawl
- Route 11
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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.
- 135 N. Cameron Street
Winchester, VA 22601 - (540) 662-3863
- thebloom.com
- 135 N. Cameron Street
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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.
- 155 Fairground Road
Clear Brook, VA 22624 - (540) 336-9114
- www.winchesterappleharvest.com
- 155 Fairground Road
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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.
- 7 N. Loudoun Street
Winchester, VA 22601 - (540) 409-7105
- skylineindiefilmfest.org
- 7 N. Loudoun Street
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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.
- 1 N. Loudoun Street
Winchester, VA 22601 - (540) 535-3660
- oldtownwinchesterva.com
- 1 N. Loudoun Street
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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.
- 1700 Amherst Street
Winchester, VA 22601 - (540) 667-1416
- dormition.va.goarch.org/greek-festival
- 1700 Amherst Street
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Winter Wonderland
Take a magical stroll through this winter wonderland light display, along a paved path in Clearbrook Park. Enjoy free hot chocolate and warm up in the cabin, where you might run into Santa. End of November-early January.
- 3300 Martinsburg Pike
Winchester, VA 22624 - (540) 665-5678
- www.fcva.us/departments/parks-recreation/special-events
- 3300 Martinsburg Pike