Annual Events
Annual Events
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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.
- Loudoun Street
Winchester, VA 22601 - (540) 535-3660
- oldtownwinchesterva.com
- Loudoun Street
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Hop Blossom Craft Beer Festival
Beer festival featuring 40+ breweries, a homebrew competition, and live music in Old Town Winchester. Mid-June.
- 124 Amherst Street
Winchester, VA 22601 - hopblossom.com
- 124 Amherst Street
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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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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, 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.
- 33 E. Boscawen Street
Winchester, VA 22601 - (540) 535-3660
- oldtownwinchesterva.com/events/major-events/oktoberfest
- 33 E. Boscawen 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