All Upcoming events

• Sun, 14 Dec, 2025 - 11:00 AM

  Yuletide Mystical Market

  Raven Conjure

  1021+ Interested
• Fri, 12 Dec, 2025 - 08:00 PM

  Winchester Holiday Lights Trolley Tour

  1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601

  247+ Interested
• Sat, 13 Dec, 2025 - 01:00 PM

  Holiday Wreath Making Workshop

  The Homestead Farm at Fruit Hill Orchard LLC

  USD 66
• Fri, 12 Dec, 2025 - 06:00 PM

  Ambrogi Acres 420 Game Nights 🟢

  187 Chickadee Lane, 22603
• Sat, 13 Dec, 2025 - 05:30 PM

  The Ghost of Christmas Past (A Paranormal Investigation)

  101 N Loudoun St, Winchester, VA

  74+ Interested
• Fri, 19 Dec, 2025 - 12:00 PM

  🎁 2nd Annual Kids Shopping Free Event at SPCA Thrift! 🎄

  1944 Abrams Creek, Winchester, VA, United States, Virginia 22601

  165+ Interested
• Sat, 13 Dec, 2025 - 05:30 PM

  Phil Kline’s Unsilent Night

  1460 University Dr, Winchester, VA, United States, Virginia 22601
• Sat, 17 Jan, 2026 - 08:00 PM

  Collin Raye in Winchester

  Backseat Events
• Fri, 30 Jan, 2026 - 06:00 PM

  Karaoke at West Oaks

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  16+ Interested
• Thu, 11 Dec, 2025 - 07:00 PM

  Swing into the Holidays with Winchester Swing Dance

  Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601

  55+ Interested
• Sat, 27 Dec, 2025 - 08:00 PM

  Cumberland Road at Bright Box Theater!

  Bright Box Theater

  33+ Interested
• Sat, 20 Dec, 2025 - 06:00 PM

  8ball Chip Tournament

  109 Fullhouse Dr, Winchester, Va, 22603

  7+ Interested
• Wed, 31 Dec, 2025 - 08:00 PM

  Blues, Brass & Bubbly: A New Year’s Eve with Terry Oates & The Mudcats

  114 Full House Drive, Winchester, VA

  127+ Interested
• Fri, 12 Dec, 2025 - 06:30 PM

  Classic French Holiday Dinner

  27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

  10+ Interested
• Sat, 13 Dec, 2025 - 07:00 PM

  "Clue Christmas" - A Murder Mystery Comedy Show // 7PM SHOW

  Bright Box Theater

  22+ Interested
• Fri, 19 Dec, 2025 - 10:00 PM

  Drag bingo at 5050 taphouse

  5050Taphouse
• Sat, 13 Dec, 2025 - 11:00 AM

  Handley Library Tour - Behind the Scenes

  100 W Piccadilly St, Winchester, VA, United States, Virginia 22601

  6+ Interested
• Thu, 11 Dec, 2025 - 06:00 PM

  Holiday Scavenger Hunt Fun Run

  Runners' Retreat

  56+ Interested
• Sat, 20 Dec, 2025 - 10:00 AM

  A Day in the Kitchen: Advanced Macaron

  27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

  4+ Interested
• Sat, 24 Jan, 2026 - 07:00 PM

  Winchester Elks Lodge - Mack Berry Band

  Elks Club

  8+ Interested
• Sat, 24 Jan, 2026 - 07:00 PM

  Rosie Soul Returns to the Blue Fox!

  Blue Fox Billiards

  86+ Interested
• Sat, 09 May, 2026 - 10:00 AM

  Beltane Luna Market 2026

  125 S. Loudoun Street, Winchester, VA

  108+ Interested
• Fri, 12 Dec, 2025 - 05:00 PM

  December Friday² Free BEER & WINE Tasting + Pop Up Market

  90 Featherbed Ln, Winchester, VA
• Sat, 20 Dec, 2025 - 03:00 PM

  Slamdance Kooperatieve with winemaker Daniel Callen

  Patti's Place

  USD 45
• Fri, 19 Dec, 2025 - 08:00 PM

  Big Hair, Bright Lights & Spank the 80s!

  114 Full House Drive, Winchester, VA

  197+ Interested
• Sat, 13 Dec, 2025 - 10:00 AM

  Pictures with Santa @ West Oaks

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  1116+ Interested
• Sat, 20 Jun, 2026 - 10:00 AM

  Litha Luna Market 2026

  125 S. Loudoun Street, Winchester, VA

  63+ Interested
• Thu, 11 Dec, 2025 - 05:00 PM

  Cow & Claus Ugly Sweater Party at Chick-fil-A

  2230 S Pleasant Valley Rd, 22601

  57+ Interested
• Fri, 23 Jan, 2026 - 06:00 PM

  Vision & Vino: A Vision Board Social - TICKET NEEDED

  2 N Kent St, Winchester, VA 22601-5038, United States
• Sat, 13 Dec, 2025 - 12:00 PM

  Santa Express

  231 E Piccadilly St, Winchester, VA, 22601

  14+ Interested
• Sat, 20 Dec, 2025 - 04:30 PM

  Christmas Dinner and The Dixie Moon Band

  1730 Berryville Pike, Winchester, VA

  12+ Interested
• Fri, 12 Dec, 2025 - 08:00 PM

  Cold Beer & Common Sense with Spencer Hatcher

  114 Full House Drive , Winchester, VA, United States, Virginia 22603

  114+ Interested
• Fri, 23 Jan, 2026 - 08:00 PM

  Emo Night Karaoke 1/23 @ Bright Box Theater

  Bright Box Theater

  USD 21
• Sat, 13 Dec, 2025 - 01:00 PM

  COCOA AND COOKIES WITH SANTA

  T-Bone's Bar & Grill

  46+ Interested
• Sat, 20 Dec, 2025 - 05:30 PM

  A DIVA's Christmas Special

  Bright Box (Winchester, VA)

  80+ Interested
• Tue, 09 Dec, 2025 - 07:30 PM

  Keith Harkin Trio - Winchester VA Bright Box Theater

  Bright Box Theater

  11+ Interested
• Fri, 16 Jan, 2026 - 08:00 PM

  BOOM! Is back at the backseat

  Backseat Bar and Grill

  17+ Interested
• Thu, 15 Jan, 2026 - 07:00 PM

  Wait Until Dark

  Winchester Little Theatre
• Sun, 06 Dec, 2026 - 10:00 AM

  Yuletide Magic Market

  105 Millwood Ave, Winchester, VA, United States, Virginia 22601

  209+ Interested
• Sat, 20 Dec, 2025 - 08:00 PM

  Backseat Winchester Va

  Backseat Bar and Grill

  124+ Interested
• Fri, 19 Dec, 2025 - 04:00 PM

  Fire Pit Fridays

  4063 Middle Rd, Winchester, VA, United States, Virginia 22602

  5+ Interested
• Fri, 12 Dec, 2025 - 06:00 PM

  Light the World

  399 Apple Pie Ridge Rd, Winchester, VA, United States, Virginia 22603

  141+ Interested
• Thu, 11 Dec, 2025 - 06:00 PM

  Trans Family Affinity Group

  124 W Piccadilly St, Winchester, VA 22601-3916, United States
• Sat, 13 Dec, 2025 - 11:00 AM

  2025 Winchester Wreaths Across America Day - Wreath Laying and Ceremony

  401 National Ave, Winchester, VA, United States, Virginia 22602

  82+ Interested
• Sat, 07 Feb, 2026 - 06:00 PM

  Someone Special Dance

  West Oaks Farm Market

  27+ Interested
• Sun, 14 Dec, 2025 - 03:00 PM

  A Christmas Carol

  Grace Evangelical Lutheran Church 26 W Boscawen St A-201, Winchester, VA 22601

  52+ Interested
• Sat, 20 Dec, 2025 - 07:00 PM

  Dirty Santa Christmas Party!

  Broken Window Brewing Co.

  42+ Interested
• Sat, 13 Dec, 2025 - 07:00 PM

  Fork In The Road @ Winchester Eagles!

  Winchester Virginia Eagles Club 824

  5+ Interested
• Sun, 04 Jan, 2026 - 12:00 PM

  Shark Pit 7-Year Anniversary Seminar

  210 Fort Collier Road, Unit 6, Winchester, VA

  91+ Interested
• Wed, 17 Dec, 2025 - 06:30 PM

  Christmas Music Bingo

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  416+ Interested
• Sat, 13 Dec, 2025 - 07:30 PM

  Flute Ensemble

  Goodson Chapel Recital Hall

  4+ Interested
• Sat, 13 Dec, 2025 - 02:00 PM

  The Nutcracker Ballet

  John Handley High School

  16+ Interested
• Sat, 13 Dec, 2025 - 04:15 PM

  Go Big and Stay Home

  Patti's Place

  USD 87
• Mon, 15 Dec, 2025 - 07:30 PM

  Chamber Brass Recital

  Goodson Chapel Recital Hall

  4+ Interested
• Sat, 17 Jan, 2026 - 08:00 PM

  Wait Until Dark at Winchester Little Theatre Inc.

  Winchester Little Theatre Inc.
• Sat, 10 Jan, 2026 - 08:00 PM

  The Amish Outlaws Return to Backseat Events in Winchester, VA

  114 Full House Drive , Winchester, VA, United States, Virginia 22603

  132+ Interested
• Sat, 13 Dec, 2025 - 06:00 PM

  Ugly Sweater Contest & Thieves Christmas!

  1730 Berryville Pike, Winchester, VA

  8+ Interested
• Fri, 12 Dec, 2025 - 08:00 PM

  The Bass Club Presents: MAD DUBZ

  Bright Box Theater

  USD 13
• Sun, 21 Dec, 2025 - 02:00 PM

  Dec 2025 Holiday Tour & Hannukah event at Peaceful Fields Sanctuary

  Peaceful Fields Sanctuary

  USD 13
• Sat, 27 Dec, 2025 - 07:00 PM

  Winchester Elks Lodge - Tuff Luck Band

  Fraternal Order of Elks Lodge 867

  11+ Interested
• Thu, 11 Dec, 2025 - 04:30 PM

  Teen Art Club

  Museum of the Shenandoah Valley
• Sun, 04 Jan, 2026 - 03:00 PM

  🟣 Scout Spark: A Sister Scout’s Social

  Winchester Brew Works
• Fri, 19 Dec, 2025 - 07:30 PM

  FLW LIVE at Piccadillys!

  Piccadilly's Public House and Restaurant

  4+ Interested
• Sun, 14 Dec, 2025 - 02:30 PM

  Van Buren Winds

  Armstrong Concert Hall
• Fri, 06 Feb, 2026 - 07:00 PM

  Winchester Elks

  466 Front Royal Pike, Winchester, VA 22602-7315, United States
• Fri, 17 Apr, 2026 - 05:00 PM

  Matriarchs of Midwifery: Wisdom, Care & Legacy

  School of Business - Shenandoah University

  74+ Interested
• Sat, 03 Jan, 2026 - 07:00 PM

  Chuggalug at our fav Winchester Elks!

  Fraternal Order of Elks Lodge 867

  10+ Interested
• Sat, 24 Jan, 2026 - 05:00 PM

  Cash Party

  250 Costello Dr, Winchester, VA 22602-4310, United States

  194+ Interested
• Sat, 03 Jan, 2026 - 09:30 AM

  SVR Winter Series Wags at West Oaks 5K and Brunch! Race and SPCA Adoption Event

  4305 Middle Road, Winchester, VA, United States, Virginia 22602

  26+ Interested
• Sat, 13 Dec, 2025 - 12:00 PM

  The Santa's Express Old Town Cookie Crawl

  Old Town Winchester Walking Mall
• Sat, 13 Dec, 2025 - 01:00 PM

  Heir and a Parent: Christmas Cookie House

  27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

  6+ Interested
• Sat, 10 Jan, 2026 - 08:00 PM

  Winter Disco Drag Show

  Winchester Brew Works

  USD 18
• Tue, 16 Dec, 2025 - 06:00 PM

  Young Adult Affinity Group

  124 W Piccadilly St, Winchester, VA 22601-3916, United States
• Wed, 28 Jan, 2026 - 07:00 PM

  Joe Nichols

  Backseat Events
• Sat, 13 Dec, 2025 - 10:00 AM

  Gourmet Cookies

  27 North Loudoun Street, Winchester, VA, United States, Virginia 22601

  14+ Interested
• Sat, 13 Dec, 2025 - 02:00 PM

  Literacy Family Holiday Party with Santa

  Winchester Public Schools

  43+ Interested
• Fri, 30 Jan, 2026 - 08:00 PM

  Jackyl in Winchester

  Backseat Events
• Sat, 13 Dec, 2025 - 11:00 AM

  The Red Gobbo Secret Gift Exchange

  255 Market Street, Winchester, VA, United States, Virginia 22603

  5+ Interested
• Sat, 17 Jan, 2026 - 08:00 AM

  University of Scouting

  James Wood High School

  32+ Interested
• Sat, 13 Dec, 2025 - 02:30 PM

  NW Works Chimers

  Armstrong Concert Hall
• Wed, 31 Dec, 2025 - 06:00 PM

  Old Town Winchester New Year's Eve Celebration 2026

  Old Town, Winchester

  141+ Interested
• Tue, 09 Dec, 2025 - 11:00 AM

  W.O.W. - Women of Winchester Christmas Jingle & Mingle

  The George Washington A Wyndham Grand Hotel

  USD 29
• Tue, 23 Dec, 2025 - 07:00 PM

  Candlelight Christmas Experience

  2870 Middle Rd, Winchester, VA, United States, Virginia 22601

  94+ Interested
• Sat, 13 Dec, 2025 - 11:00 AM

  Guest Reading: Miss Elizabeth’s Tarot

  125 S. Loudoun Street, Winchester, VA

  7+ Interested
• Tue, 16 Dec, 2025 - 06:30 PM

  Legacy Christian Academy Christmas Concert

  Daniel Morgan Middle School

  Free
• Sat, 28 Feb, 2026 - 08:00 PM

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

  Winchester Brew Works

  USD 18
• Sun, 28 Dec, 2025 - 04:25 PM

  The Philadelphia Eagles vs the Buffalo Bills: Live at The Cider House

  30 East Piccadilly Street, Winchester, VA, United States, Virginia 22601
• Thu, 29 Jan, 2026 - 08:00 PM

  Backseat Events - Joe Nichols - Mack Berry Band

  Backseat Events

  41+ Interested
• Sat, 03 Jan, 2026 - 09:30 AM

  2025-2026 Winter Series #3 - Wags at West Oaks Farmers Market

  West Oaks Farm Market
• Wed, 17 Dec, 2025 - 09:00 AM

  Wee One's Wednesdays

  1001 E Cork St, Winchester, VA, United States, Virginia 22601
• Sun, 21 Dec, 2025 - 06:00 PM

  14th Annual Beer & Carols Celebration

  Piccadilly's Public House and Restaurant

  20+ Interested
• Wed, 10 Dec, 2025 - 09:30 AM

  Slow Flow with Brandie

  420 W Jubal Early Drive, Suite 105, Winchester, VA
• Tue, 16 Dec, 2025 - 12:00 PM

  WINCHESTER🦞at APPLE BLOSSOM MALL (Opposite JCPenny)

  1850 Apple Blossom Dr, Winchester, VA 22601

  7+ Interested
• Sat, 13 Dec, 2025 - 09:00 AM

  Rack 'Em Billiards 550 & Under 9Ball

  109 Full House Dr, Winchester, VA 22603-4671, United States

  36+ Interested
• Tue, 16 Dec, 2025 - 04:30 PM

  FREE Prenatal Yoga

  301 N Cameron St, Ste 101, Winchester, VA, United States, Virginia 22601
• Fri, 16 Jan, 2026 - 06:00 PM

  Steak Dinner & Live Music from Those 3 Guys

  4305 Middle Road, Winchester, VA, United States, Virginia 22602
• Sat, 17 Jan, 2026 - 11:00 AM

  One Year Downtown Celebration

  125 S. Loudoun Street, Winchester, VA

  87+ Interested
• Sat, 13 Dec, 2025 - 02:30 PM

  NW Works Chimers Concert

  Armstrong Concert Hall

  13+ Interested
• Tue, 09 Dec, 2025 - 06:30 PM

  Thrifty TUESDAY Paint Night $25 Paint Night at Easely Created

  Easely Created Winchester

  7+ Interested