Winchester Food & Drink Events

United Bank Bloomin' Wine Fest

Downtown Walking Mall 24 Apr 2026

United Bank Bloomin' Wine Fest

Downtown Walking Mall 25 Apr 2026

Strawberry Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 23 May 2026

Peach Festival

3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 8 Aug 2026

Sunflower Festival

2502 N. Frederick Pike, Winchester, VA 12 Sep 2026

NAACP Winchester Area Juneteenth 2026

Museum of the Shenandoah Valley 14 Jun 2026

Hop Blossom Craft Beer Festival 2026

Old Town Winchester 6 Jun 2026

Apple Harvest Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 3 Oct 2026

New Playground Grand Opening Event

Winchester VA Parks and Recreation 18 Apr 2026

Peaches & Beaches Festival

4305 Middle Road, Winchester, VA, United States, Virginia 22602 1 Aug 2026

Navy Federal Credit Union Veterans Dinner Show

James R. Wilkins, Jr. Athletic & Events Center 29 Apr 2026

West Oaks Bloomin' Brunch and Bubbly 2026

4305 Middle Road, Winchester, VA, United States, Virginia 22602 26 Apr 2026

Valley Cycle Center Stag Luncheon

Winchester Cold Storage / WCS Logistics 1 May 2026

Empanadas & Wine Pairing

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 25 Apr 2026

Honeycrisp Festival

3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602 5 Sep 2026

Taste of Community Food Truck Festival

1460 University Dr, Winchester, VA 22601, United States 16 May 2026

VA250 Fireworks Celebration

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 11 Jul 2026

Mother’s Day Cheesecake Pairing

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 9 May 2026

Corks & Cakes

4063 Middle Rd, Winchester, VA, United States, Virginia 22602 20 Jun 2026

2026 Winchester Greek Festival

1700 Amherst St, Winchester, VA, United States, Virginia 22601 22 Aug 2026

Car Show

Armel Elementary School 18 Apr 2026

Mother's Day Brunch at Patti’s Place

Patti's Place 10 May 2026

Sip & Sourdough™ – WASPCA Benefit

Winchester Area SPCA 19 Apr 2026

Cooking with Kimchi

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 26 Apr 2026

Pierogies!

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 13 Jun 2026

Breaking Bread

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 13 Jun 2026

If the Choux Fits

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 21 Apr 2026

Bloom Boom!

608 Millwood Ave, Winchester, VA 22601-5167, United States 2 May 2026

Winchester Local & international market

Winchester Moose Lodge 1283 25 Apr 2026

Brunch Around the World

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 17 Apr 2026

Local Plants & Local Pints at WBW

320 N Cameron St, Winchester, VA 25 Apr 2026

Cinco de Mayo Favorites

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 5 May 2026

Kubota Orange Days at Winchester Equipment

121 Indian Hollow Rd, Winchester, VA, United States, Virginia 22603 25 Apr 2026

KIWANIS PANCAKE DAY to BENEFIT IJMM

War Memorial Building, Jim Barnett Park 25 Apr 2026

The French Pantry

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 12 May 2026

Bluegrass on the Farm

2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603 11 Jun 2026

Glow All Out 5K

Admiral Richard E. Byrd Middle School 17 Jul 2026

WildKind Open Table · May

Broken Window Brewing Co. 3 May 2026

Music Jam on the Farm, Phelpsmore Lane

303 Phelpsmore Ln, Winchester, VA 22602-2074, United States 1 May 2026