Food & Drink events in Winchester

Check out happening food & drink events all around Winchester, VA

Strawberry Festival

Sat, 23 May at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Peach Festival

 Sat, 08 Aug at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Sunflower Festival

Sat, 12 Sep at 10:00 am 2502 N. Frederick Pike, Winchester, VA

NAACP Winchester Area Juneteenth 2026

 Sun, 14 Jun at 12:00 pm Museum of the Shenandoah Valley

Hop Blossom Craft Beer Festival 2026

 Sat, 06 Jun at 12:00 pm Old Town Winchester USD 7 to 39

Navy Federal Credit Union Veterans Dinner Show

 Wed, 29 Apr at 06:00 pm James R. Wilkins, Jr. Athletic & Events Center

Valley Cycle Center Stag Luncheon

 Fri, 01 May at 11:45 am Winchester Cold Storage / WCS Logistics

Apple Harvest Festival

Sat, 03 Oct at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Homestead Harvest Festival

Sat, 24 Oct at 10:00 am 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

Peaches & Beaches Festival

Sat, 01 Aug at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Bloomin' Brews & Boogie

 Fri, 01 May at 12:00 pm 145 N Loudoun St, Winchester, VA 22601-4717, United States

Apple Harvest Festival

 Sat, 10 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Honeycrisp Festival

 Sat, 05 Sep at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Mother’s Day Cheesecake Pairing

 Sat, 09 May at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Taste of Community Food Truck Festival

 Sat, 16 May at 11:00 am 1460 University Dr, Winchester, VA 22601, United States

VA250 Fireworks Celebration

 Sat, 11 Jul at 08:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Pumpkin Festival

 Sat, 24 Oct at 09:00 am 3035 Cedar Creek Grade, Winchester, VA, United States, Virginia 22602

Corks & Cakes

 Sat, 20 Jun at 01:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

2026 Winchester Greek Festival

Sat, 22 Aug at 11:00 am 1700 Amherst St, Winchester, VA, United States, Virginia 22601

Mother's Day Brunch at Patti’s Place

 Sun, 10 May at 11:00 am Patti's Place USD 45

Apple Pie Baking Contest

 Thu, 30 Apr at 09:00 am Marker-Miller Orchards Farm Market

Pierogies!

 Sat, 13 Jun at 04:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Bloom After Dark w/ DJ OPHIE & DJ CURFEW

 Fri, 01 May at 09:00 pm Bright Box Theater

Bloom Boom!

 Sat, 02 May at 07:00 pm 608 Millwood Ave, Winchester, VA 22601-5167, United States

Breaking Bread

 Sat, 13 Jun at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Live Music: Six Strings & Bourbon

 Sun, 17 May at 01:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Tea Party Treats

 Sat, 23 May at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Cinco de Mayo Favorites

 Tue, 05 May at 06:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

The French Pantry

 Tue, 12 May at 06:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Bluegrass on the Farm

 Thu, 11 Jun at 06:00 pm 2502 N. Frederick Pike , Winchester, VA, United States, Virginia 22603

Glow All Out 5K

 Fri, 17 Jul at 08:00 pm Admiral Richard E. Byrd Middle School

WildKind Open Table · May

 Sun, 03 May at 03:00 pm Broken Window Brewing Co.

Music Jam on the Farm, Phelpsmore Lane

 Fri, 01 May at 06:00 pm 303 Phelpsmore Ln, Winchester, VA 22602-2074, United States

MoveMentation's FUN-raiser

 Sat, 11 Jul at 05:00 pm 740 Merrimans Ln, Winchester, VA 22601, United States