Upcoming Winchester Events

Check out what's happening all around Winchester, VA

Good Times & Great Country - Joe Nichols LIVE at Backseat Events!

 Thu, 29 Jan at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Claudio’s Pizzeria Friday Night Fever Disco Dance Party

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

Jackyl in Winchester

 Fri, 30 Jan at 08:00 pm Backseat Events

Joe Nichols, Mack Berry Band in Winchester

 Thu, 29 Jan at 08:00 pm Backseat Events

Strawberry Festival

Sat, 23 May at 11:00 am 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

Valentine's Day Dinner

 Sat, 14 Feb at 05:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

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

Couples Therapy: A Comedy Show hosted by Rahmein Mostafavi

 Fri, 13 Feb at 08:00 pm Bright Box Theater

Galentine's Night Out: Paint & Sip!

 Thu, 12 Feb at 06:00 pm 302 S Loudoun Street, Winchester, VA

Get Your Dreams On — Tell Me Lies: The Fleetwood Mac Experience

 Fri, 06 Feb at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Love Letters Evening

 Sat, 14 Feb at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

66th Annual Apple Blossom Antique Car Meet

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

FREE COMMUNITY DANCE NIGHT!

Thu, 19 Feb at 07:00 pm 10 N Kent St, Winchester, VA, United States, Virginia 22601

Someone Special Dance | presented by Finch Oral & Facial Surgery

 Sat, 07 Feb at 06:00 pm West Oaks Farm Market

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

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

Emo Night Karaoke 1/23 @ Bright Box Theater

 Fri, 23 Jan at 08:00 pm Bright Box Theater USD 21

Ambrogi Acres 2nd Annual 420 Event

 Sat, 18 Apr at 12:00 pm Backseat Events

Kids Festival

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

Bourbon Pairing Dinner featuring Brothers Bond Bourbon at UNO Winchester

 Mon, 02 Feb at 06:00 pm UNO Pizzeria & Grill USD 65

Joe Nichols

 Wed, 28 Jan at 07:00 pm Backseat Events

For the Love of Linda: Honoring the Music of Linda Ronstadt

 Fri, 20 Feb at 08:00 pm Bright Box Theater

Spring Bridal Expo 2026

 Sun, 01 Mar at 12:00 pm The George Washington Hotel

Cash Party

 Sat, 24 Jan at 05:00 pm 250 Costello Dr, Winchester, VA 22602-4310, United States

Glazed and Confused

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

FredCo Eats Restaurant Week 2026

 Mon, 26 Jan at 07:00 am Various Locations Across Frederick County, Virginia

Vibrissa's Got Talent!

Sat, 07 Feb at 08:00 pm Vibrissa Beer (Winchester, VA)

Maker Day: Mugs

 Sat, 07 Feb at 10:00 am 901 Amherst St, Winchester, VA, United States, Virginia 22601

Winchester Swing Dance Lesson & Social Dancing

 Thu, 22 Jan at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Bright Box Comedy: Ryan Donahue (7PM SHOW)

 Sat, 31 Jan at 07:00 pm Bright Box (Winchester, VA)

Mindfulness Meet-Up at Please Boutique

 Sat, 24 Jan at 11:00 am 2214 Wilson Blvd Winchester, VA 22601

Beltane Luna Market 2026

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

Western Swing Dance Night

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

Joey Harkum w/ The Grilled Lincolns

 Thu, 05 Feb at 07:00 pm Bright Box Theater

Bridgerton

Fri, 30 Jan at 06:00 pm 157 N Loudoun St, Winchester, VA, United States, Virginia 22601

Practical Tai Chi

Sat, 24 Jan at 11:00 am First Presbyterian Church of Winchester, Virginia

James & Joel: Great American Songwriters

 Sun, 22 Feb at 03:30 pm Bright Box Theater

Sausage Gravy Cook Off Benefiting Friends of Old Town

 Sat, 31 Jan at 02:00 pm 320 N Cameron St, Winchester, VA, United States, Virginia 22601

Beginners' Yang-style Tai Chi

Sat, 24 Jan at 09:30 am First Presbyterian Church of Winchester, Virginia

Sourdough, Stitch & Sip

 Sat, 24 Jan at 01:00 pm Valerie Hill Vineyard & Winery

WATTS Coldest Night of the Year

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

An Evening with Stephane Wrembel

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

Malevolent #1 World Premiere with Justin Jordan and Ben Templesmith!

 Wed, 28 Jan at 04:00 pm 80 Weems Ln, Winchester, VA, United States, Virginia 22601

Rosie Soul Returns to the Blue Fox!

Sat, 24 Jan at 07:00 pm Blue Fox Billiards

Comedy Night at James Charles Winery

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

Anything But A Cup Party!

 Sat, 24 Jan at 02:00 pm 320 N Cameron St, Winchester, VA

Mindfulness Meet-Up at Please Boutique

Sat, 31 Jan at 11:00 am 2214 Wilson Blvd Winchester, VA 22601

Cornhole Blind Draw Tournament

Thu, 22 Jan at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Sweethearts Swing Dance

 Thu, 12 Feb at 07:00 pm Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

Light a Path to end pet homelessness

Mon, 02 Feb at 06:15 pm 111 Featherbed Lane, Winchester, VA, United States, Virginia 22601

First Cat Cave Crochet Circle of 2026

 Fri, 23 Jan at 02:30 pm 111 Featherbed Lane, Winchester, VA

Why Food Co-ops: How to tell our story (really) well!

 Tue, 27 Jan at 05:30 pm Our Health Free

Jackyl — Chainsaws, Southern Rock and Loud Guitars

 Fri, 30 Jan at 08:00 pm 114 Full House Drive , Winchester, VA, United States, Virginia 22603

Game On Saturdays for Teens at Handley Library!

 Sat, 31 Jan at 01:30 pm 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

Wee One's Wednesdays

 Wed, 21 Jan at 09:00 am 1001 E Cork St, Winchester, VA, United States, Virginia 22601

Evans Home's Annual Chili Dinner

 Fri, 13 Feb at 05:00 pm Braddock Street United Methodist Church

Lincoln Reagan Dinner

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

2026 Museum of Shenandoah Valley 5k/10k

 Sat, 07 Feb at 08:30 am 901 Amherst St, Winchester, VA 22601-3305, United States

Spring Equinox Luna Market 2026

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

Live Music with Brad the Guitar Guy

 Sat, 24 Jan at 02:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Learn Herbal Medicine Techniques for Upper Respiratory Relief

 Sun, 25 Jan at 02:30 pm Patti's Place USD 15

90s & 00s Night @ Backseat Bar & Grill

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

Feb Volunteer Day at Peaceful Fields Sanctuary

 Sun, 01 Feb at 11:00 am Peaceful Fields Sanctuary

Book Signing for The Day it Rained Popcorn

 Sat, 21 Feb at 11:00 am Winchester Book Gallery

Petsmart Adoption Event (KITTENS)

 Sat, 24 Jan at 12:00 pm PetSmart (Winchester, VA)

Galentine’s Night @K.Noel & Co.

 Thu, 05 Feb at 06:00 pm 161 Prosperity Dr Ste. 101, Winchester, VA

Unpacking GSM Blends: A Wine Tasting with Tablas Creek

 Sat, 31 Jan at 04:15 pm Patti's Place USD 75

Hanging Out With Tuck: DYING WITH A SECRET at Solenberger’s Hardware

 Sat, 31 Jan at 11:00 am Solenberger's Home & Hardware

Galentines Paint & Sip!

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

Valentine’s & Galentine’s Brunch at Patti’s Place

 Sat, 14 Feb at 11:00 am Patti's Place USD 75

Chocolate Festival

 Sat, 07 Feb at 11:00 am 115 Wolfe St, 22601

Trivia Night with Route 11 DJ

 Fri, 23 Jan at 07:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602

Spaghtti Dinner Buffet & Music from Allen Boyd & The Waysiders

 Fri, 23 Jan at 06:00 pm 4305 Middle Road, Winchester, VA, United States, Virginia 22602

Thrift on Tap at DCBC: A Chocolate Escape Sip & Shop

 Sat, 07 Feb at 12:00 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

Better Human Book Club

Wed, 04 Feb at 06:30 pm Handley Regional Library System

Guest Reading: Mad Hatter Tarot

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

Wombful Wisdom Workshop

 Mon, 26 Jan at 05:30 pm Sage Center for Women's Health

Paella Day

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

NAACP Winchester Area Branch General Meeting

 Sat, 14 Feb at 09:30 am Winchester Public Schools

Bug Pinning with Tiny World Jars

Sat, 21 Feb at 01:00 pm 125 S. Loudoun Street, Winchester, VA

Anti-Valentine's Day Trivia @ DCBC!

 Wed, 11 Feb at 07:30 pm 160 N Loudoun St, Winchester, VA, United States, Virginia 22601

Publishing the Past: A Miserable Revenge

 Sun, 01 Feb at 03:00 pm 901 Amherst St, Winchester, VA, United States, Virginia 22601

Community Closet by Connected Communities

 Sun, 25 Jan at 12:00 pm 2654 Valley Ave, Suite B , Winchester, VA, United States, Virginia 22601

Large Group, Small Share Groups & Crosstalk Café

 Thu, 22 Jan at 06:30 pm 181 Nazarene Dr, Winchester, VA, United States, Virginia 22601

Litha Luna Market 2026

 Sat, 20 Jun at 10:00 am 125 S. Loudoun Street, Winchester, VA

Spin to Win-chester Fundraiser

 Sat, 21 Feb at 01:00 pm Valley Health Wellness & Fitness Center

Winchester - Virginia Concealed Carry Class - $55

 Mon, 26 Jan at 06:00 pm La Quinta Inn & Suites Winchester

Cozy Writing Workshop

 Sat, 21 Feb at 02:00 pm 124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601

Ultimate Soup-er Bowl Bash

 Sat, 07 Feb at 02:00 pm Winchester Brew Works

Friends of Old Town Community Meeting

 Wed, 18 Feb at 06:00 pm Handley Regional Library System

Design Detox

 Thu, 29 Jan at 05:00 pm 224 S Loudoun St, Winchester, VA

Bakers & Artisans Handmade Pop Up

Fri, 06 Feb at 11:00 am 42 E. Piccadilly Street, Winchester, VA

Petsmart Adoption Event (KITTENS)

 Sat, 07 Feb at 12:00 pm PetSmart (Winchester, VA)

Dancing Thru the Decades

 Sat, 07 Feb at 06:00 pm Backseat Events

Malloy Toyota Country Music Party

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

Readings With Chrystal

Sun, 01 Feb at 12:00 pm 105 Millwood Ave, Winchester, VA

📚 Children’s Book Reading with Local Author, Dianne Rigby

 Sun, 25 Jan at 01:00 pm 1944 Abrams Creek, Winchester, VA, United States, Virginia 22601

Easter Breads

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

Craft Nights at Chilly Hollow Brewery - Handknit Heart Pillow

 Fri, 13 Feb at 06:00 pm Easely Created Winchester

MotherBaby Circles

 Thu, 22 Jan at 10:00 am Sage Center for Women's Health
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