Upcoming Winchester Events

Check out what's happening all around Winchester, VA

Celtic Fest

 Sat, 14 Mar at 12:00 pm Old Town Winchester

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

 Fri, 01 May at 09:00 pm James R. Wilkins, Jr. Athletic & Events Center

HoneyWay Apple Blossom Golf Classic

 Fri, 24 Apr at 12:00 pm Rock Harbor Golf Course

West Oaks 7th Annual Adult Egg Hunt

 Sun, 29 Mar at 12:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Carter Myers Automotive Jimmy Buffett Tribute Show

 Thu, 30 Apr at 07:00 pm James R. Wilkins, Jr. Athletic & Events Center

Strawberry Festival

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

Flashlight Egg Hunt

 Fri, 20 Mar at 06:30 pm 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Coronation of Queen Shenandoah

 Fri, 01 May at 01:30 pm John Handley High School

First Bank Men's Commonwealth Luncheon

 Fri, 01 May at 11:00 am Piccadilly's Public House and Restaurant

Country Nite @ Bright Box Theater in Winchester, VA

 Fri, 06 Mar at 07:00 pm Bright Box Theater USD 18 to 82

Shades of HUNKS at Winchester Brew Works (Winchester, VA) 02/28/26

 Sat, 28 Feb at 08:00 pm Winchester Brew Works USD 18 to 79

Jackyl in Winchester

 Thu, 09 Apr at 08:00 pm Backseat Events

First Friday

 Fri, 07 Aug at 05:00 pm Old Town Winchester Walking Mall

Peaches & Beaches Festival

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

An Evening with Stephane Wrembel

 Fri, 27 Feb at 08:00 pm Bright Box (Winchester, VA)

32nd Annual Valley Health Community Wellness Festival

 Sat, 28 Feb at 10:00 am Apple Blossom Mall

Hop Blossom Craft Beer Festival 2026

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

West Oaks Spring Vendor Fair 2026

 Sat, 04 Apr at 09:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Rhea Lana's of Winchester Spring/Summer Family Shopping Event!

 Wed, 18 Mar at 04:30 pm 221 Commonwealth Ct, Winchester, VA 22602, USA

For Whom the Bell Tolls: The Four Horsemen

 Sat, 21 Mar at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Tracy Byrd in Winchester

 Fri, 17 Apr at 07:00 pm

New Playground Grand Opening Event

 Sat, 18 Apr at 11:00 am Winchester VA Parks and Recreation

90s & 00s Night @ Backseat Bar & Grill

 Sat, 18 Apr at 08:30 pm Backseat Bar and Grill

Spring Bridal Expo 2026

 Sun, 22 Mar at 12:00 pm The George Washington Hotel

66th Annual Apple Blossom Antique Car Meet

 Sat, 09 May at 08:00 am Jim Barnett Park

Little Chefs Sauce Lab at Chick-fil-A

 Wed, 18 Mar at 04:00 pm Chick-fil-A Pleasant Valley Road (2230 S Pleasant Valley Rd, )

🍀🎻 Saint Patrick’s Party at West Oaks! 🎻🍀

 Fri, 13 Mar at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Kids Festival

Sat, 27 Jun at 11:00 am 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Jackyl — Chainsaws, Southern Rock and Loud Guitars

 Thu, 09 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

First Friday

 Fri, 05 Jun at 05:00 pm Old Town Winchester

Valley Health Business at the Bloom

 Wed, 29 Apr at 11:00 am James R. Wilkins, Jr. Athletic & Events Center

Backseat Rocks with That Arena Rock Show

 Sat, 11 Apr at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

First Friday

 Fri, 03 Jul at 05:00 pm Old Town Winchester

Navy Federal Credit Union Veterans Dinner Show

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

Cash Party

 Sat, 21 Mar at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

McDonald's Apple Blossom Gaming Festival

 Sat, 25 Apr at 10:00 am 608 Millwood Ave, Winchester, VA 22601-5167, United States

Valley Cycle Center Stag Luncheon

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

Guest Reading: Mad Hatter Tarot

Sat, 07 Mar at 11:00 am 125 S. Loudoun Street, Winchester, VA

Glazed and Confused

 Sat, 14 Mar at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Bright Box Card Bazaar: An Indoor Pokemon Vendor Show

 Sat, 09 May at 09:00 am Bright Box (Winchester, VA)

Miss Honorary Fire Chief Contest

 Sat, 14 Mar at 07:00 pm James Wood Middle School

West Oaks Farm Market's 2026 Spring Vendor Fair

 Sat, 04 Apr at 09:00 am West Oaks Farm Market

Catch Me If You Can

 Thu, 26 Feb at 07:30 pm Ohrstrom-Bryant Theatre

Valerie Hill Ghost Hunt, Stephens City, Virginia

 Sat, 14 Mar at 08:00 pm Valerie Hill Vineyard & Winery

VA250 Fireworks Celebration

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

ABC Saturday! at Handley Library

 Sat, 07 Mar at 11:00 am 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

Guest Reading: Mad Hatter Tarot

Sat, 28 Feb at 11:00 am 125 S. Loudoun Street, Winchester, VA

Guest Reading: Mad Hatter Tarot

Sat, 21 Mar at 11:00 am 125 S. Loudoun Street, Winchester, VA

The Employer Expo - Regional Hiring Fair

 Wed, 13 May at 01:00 pm James R. Wilkins, Jr. Athletic & Events Center

SAVE THE DATE: Queer Prom - May 30th

 Sat, 30 May at 07:00 pm Museum of the Shenandoah Valley

Guest Reading: Half Tail Tarot

Sat, 28 Mar at 11:00 am 125 S. Loudoun Street, Winchester, VA

Country Nite @ Crooked Run Fermentation in Sterling, VA

 Sat, 28 Mar at 07:00 pm Bright Box Theater USD 18 to 82

Beltane Luna Market 2026

 Sat, 09 May at 10:00 am 125 S. Loudoun Street, Winchester, VA

Western Swing Dance Night

 Fri, 06 Mar at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Wood Badge Reunion Dinner 2026

 Sat, 28 Feb at 05:30 pm 2863 Millwood Pike, Winchester, VA 22602-4650, United States

Spring Equinox Luna Market 2026

 Sat, 11 Apr at 10:00 am 125 S. Loudoun Street, Winchester, VA

Lincoln Reagan Dinner

 Sat, 28 Mar at 06:00 pm Winchester Country Club USD 0 to 1,602

United Bank Bloomin' Wine Fest

 Fri, 24 Apr at 03:00 pm Downtown Walking Mall

Willie Watson

 Fri, 10 Apr at 07:00 pm Bright Box Theater - VA

The All Access Dance Party | Apple Blossom Festival Weekend

 Fri, 01 May at 07:00 pm Backseat Events USA USD 18 to 77

United Bank Bloomin' Wine Fest

 Sat, 25 Apr at 11:00 am Downtown Walking Mall

Malloy Toyota Country Music Party

 Sat, 02 May at 08:00 pm James R. Wilkins, Jr. Athletic & Events Center

Guest Reading: Kindred Roots Tarot

Sat, 04 Apr at 11:00 am 125 S. Loudoun Street, Winchester, VA

Comedy Night at James Charles Winery

 Sat, 21 Mar at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Full Moon Night: The Worm Moon

Tue, 03 Mar at 06:00 pm 125 S. Loudoun Street, Winchester, VA

Micro Wrestling: Winchester, VA!

 Fri, 15 May at 08:00 pm Backseat Events

Harry Potter and the Goblet of Fire Movie Trivia

 Wed, 11 Mar at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

WATTS Coldest Night of the Year

 Sat, 28 Feb at 04:00 pm 115 Wolfe St, Winchester, VA 22601-4133, United States

Paella Day

 Sat, 28 Feb at 12:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

5AM Trio: Esoterra Tour

 Thu, 26 Mar at 08:00 pm Bright Box Theater

Trivia Night

 Fri, 27 Mar at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Car Show

 Sat, 18 Apr at 10:00 am Armel Elementary School

Rise Orthodontic Studio Blossoms & Bubbles with Miss Apple Blossom

 Sun, 26 Apr at 02:30 pm Museum of the Shenandoah Valley

March Madness

 Sat, 21 Mar at 12:00 am James R. Wilkins, Jr. Athletic & Events Center

Willows At Meadow Branch Young at Heart Dance

 Thu, 30 Apr at 11:00 am Millwood Station Banquet Hall

Succulent Bowl Workshop

 Sat, 28 Feb at 02:00 pm Weber's Nursery & Garden Center

Thai Cooking Class

 Sat, 14 Mar at 12:00 pm Solenberger's Home & Hardware

Our Town

 Thu, 26 Mar at 07:30 pm Glaize Studio Theatre

Wee One's Wednesdays

 Wed, 04 Mar at 09:30 am 1001 E Cork St, Winchester, VA, United States, Virginia 22601

2026 Inspiring Tourism Summit

 Wed, 25 Feb at 08:30 am HIVE — Hub for Innovators, Veterans and Entrepreneurs Free

Final Round of the Student Soloists Competition

 Sun, 01 Mar at 02:30 pm Armstrong Concert Hall

Easter Breads

 Sat, 28 Mar at 04:30 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

Seinfeld Trivia @ DCBC!

 Wed, 25 Mar at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

Bump & Run

 Sat, 04 Apr at 12:00 am James R. Wilkins, Jr. Athletic & Events Center

A1A - Shenandoah Apple Blossom Festival - Winchester, VA

 Thu, 30 Apr at 08:00 pm Shenandoah Apple Blossom Festival®

Farm to Table Dinner and Auction

 Sat, 07 Mar at 05:30 pm West Oaks Farm Market

Unpacking GSM Blends: A Wine Tasting with Tablas Creek

 Sat, 28 Feb at 04:15 pm Patti's Place USD 75

THE BASS CLUB PRESENTS: HE$H

 Sat, 28 Feb at 08:00 pm Bright Box Theater USD 13 to 29

2026 Heatwave Hustle 5k/10k

 Sun, 28 Jun at 08:30 am 901 Amherst St, Winchester, VA 22601-3305, United States

90's Nickelodeon Trivia @ DCBC!

 Wed, 08 Apr at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

30 Years of The Reagan Years!

 Fri, 08 May at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Decision Height at Winchester Little Theatre Inc.

 Fri, 13 Mar at 08:00 pm Winchester Little Theatre Inc.

Celebrating Black History Month: History & Cocktails Night

 Thu, 26 Feb at 06:00 pm Bright Box (Winchester, VA)

W.O.W. - March Networking Event

 Tue, 10 Mar at 11:00 am The George Washington A Wyndham Grand Hotel USD 34 to 82

Tasting with Misty Mountain Meadworks

 Sat, 14 Mar at 12:00 pm Murphy Beverage Company

Pajama Party | Ladies Night Out

 Sat, 09 May at 06:00 pm The George Washington A Wyndham Grand Hotel USD 89 to 120

Record Store Day 2026 at Back to the Media

 Sat, 18 Apr at 09:00 am 48 South Loudoun St., Winchester, VA, United States, Virginia 22601

Chaos Welding and Fabrication 101 & 201

 Sat, 14 Mar at 09:00 am 344 Victory Rd, Winchester, VA, United States, Virginia 22602

Greener Living Day

 Sat, 25 Apr at 10:00 am 302 S Loudoun Street, Winchester, VA
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