Annual Events
Annual Events
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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.
- 33 E. Boscawen Street
Winchester, VA 22601 - (540) 535-3660
- oldtownwinchesterva.com/events/major-events/kidz-fest
- 33 E. Boscawen Street
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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.
- Main Street
Middletown, VA 22645 - (540) 869-2226
- www.facebook.com/pg/MiddletownVA4th
- Main Street
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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.
- Main Street
Middletown, VA 22645 - facebook.com/MiddletownVA4th
- Main Street
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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.
- 480 Chalybeate Spring Road
Winchester, VA 22603 - www.n-ssa.org
- 480 Chalybeate Spring Road
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New Year’s Eve Countdown and Apple Drop
Celebrate in Old Town Winchester with a countdown and “apple drop” to ring in the New Year on December 31.
- 15 N. Cameron Street
Winchester, VA 22601 - oldtownwinchesterva.com
- 15 N. Cameron Street
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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.
- 5165 Main Street
Stephens City, VA 22655 - (540) 869-3087
- stephenscity.vi.virginia.gov/NHF/index.shtml
- 5165 Main Street
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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
- 336 Belle Grove Road
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Oktoberfest
Taste German-inspired food, enjoy beer tastings and live music. September.
- 1 N. Loudoun Street
Winchester, VA 22601 - (540) 535-3660
- oldtownwinchesterva.com
- 1 N. Loudoun Street
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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
- Piccadilly Street at Cameron to Braddock to Cork at Loudoun
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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.
- 608 S. Kent Street
Winchester, VA 22601 - (540) 662-5555
- www.facebook.com/PatsyClineMusicFestival
- 608 S. Kent Street