Upcoming Winchester Events
Check out what's happening all around Winchester, VA
Yuletide Mystical Market
Sun, 14 Dec at 11:00 am
Raven Conjure
Winchester Holiday Lights Trolley Tour
Fri, 12 Dec at 08:00 pm
1400 S Pleasant Valley Rd, Winchester, VA, United States, Virginia 22601
Holiday Wreath Making Workshop
Sat, 13 Dec at 01:00 pm
The Homestead Farm at Fruit Hill Orchard LLC
USD 66
The Ghost of Christmas Past (A Paranormal Investigation)
Sat, 13 Dec at 05:30 pm
101 N Loudoun St, Winchester, VA
Ambrogi Acres 420 Game Nights 🟢
Fri, 12 Dec at 06:00 pm
187 Chickadee Lane, 22603
🎁 2nd Annual Kids Shopping Free Event at SPCA Thrift! 🎄
Sat, 20 Dec at 10:00 am
1944 Abrams Creek, Winchester, VA, United States, Virginia 22601
Cousins Maine Lobster
Sun, 14 Dec at 12:00 pm
4063 Middle Rd, Winchester, VA, United States, Virginia 22602
Collin Raye in Winchester
Sat, 17 Jan at 08:00 pm
Backseat Events
Phil Kline’s Unsilent Night
Sat, 13 Dec at 05:30 pm
1460 University Dr, Winchester, VA, United States, Virginia 22601
Karaoke at West Oaks
Fri, 30 Jan at 06:00 pm
4305 Middle Road, Winchester, VA, United States, Virginia 22602
"Clue Christmas" - A Murder Mystery Comedy Show // 7PM SHOW
Sat, 13 Dec at 07:00 pm
Bright Box Theater
8ball Chip Tournament
Sat, 20 Dec at 06:00 pm
109 Fullhouse Dr, Winchester, Va, 22603
Swing into the Holidays with Winchester Swing Dance
Thu, 11 Dec at 07:00 pm
Shenandoah University Hazel Pruitt Armory, 608 Millwood Ave, Winchester, VA 22601
Cumberland Road at Bright Box Theater!
Sat, 27 Dec at 08:00 pm
Bright Box Theater
Blues, Brass & Bubbly: A New Year’s Eve with Terry Oates & The Mudcats
Wed, 31 Dec at 08:00 pm
114 Full House Drive, Winchester, VA
Classic French Holiday Dinner
Fri, 12 Dec at 06:30 pm
27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
Drag bingo at 5050 taphouse
Fri, 19 Dec at 10:00 pm
5050Taphouse
Handley Library Tour - Behind the Scenes
Sat, 13 Dec at 11:00 am
100 W Piccadilly St, Winchester, VA, United States, Virginia 22601
A Day in the Kitchen: Advanced Macaron
Sat, 20 Dec at 10:00 am
27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
Elizabeth's Furnace - Return to Backseat Bar & Grill
Sat, 31 Jan at 08:30 pm
Backseat Bar and Grill
Holiday Scavenger Hunt Fun Run
Thu, 11 Dec at 06:00 pm
Runners' Retreat
Winchester Moose NYE Celebration - Tuff Luck Band
Wed, 31 Dec at 06:00 pm
Winchester Moose Lodge 1283
Pictures with Santa @ West Oaks
Sat, 13 Dec at 10:00 am
4305 Middle Road, Winchester, VA, United States, Virginia 22602
Weekly Beer Tasting at Shawnee Springs Market, Senseny Road
Fri, 12 Dec at 04:00 pm
Shawnee Springs Market & Cannery (Winchester, VA)
Winchester Elks Lodge - Mack Berry Band
Sat, 24 Jan at 07:00 pm
Elks Club
Dirty Santa Christmas Party!
Sat, 20 Dec at 07:00 pm
Broken Window Brewing Co.
Rosie Soul Returns to the Blue Fox!
Sat, 24 Jan at 07:00 pm
Blue Fox Billiards
Beltane Luna Market 2026
Sat, 09 May at 10:00 am
125 S. Loudoun Street, Winchester, VA
Slamdance Kooperatieve with winemaker Daniel Callen
Sat, 20 Dec at 03:00 pm
Patti's Place
USD 45
Big Hair, Bright Lights & Spank the 80s!
Fri, 19 Dec at 08:00 pm
114 Full House Drive, Winchester, VA
Winter Solstice Ritual Meditation with Phoenix
Sat, 20 Dec at 02:00 pm
125 S. Loudoun Street, Winchester, VA
Gallery Explorers: Winter Landscape Holiday Cards
Sat, 20 Dec at 10:30 am
901 Amherst St, Winchester, VA, United States, Virginia 22601
Cow & Claus Ugly Sweater Party at Chick-fil-A
Thu, 11 Dec at 05:00 pm
2230 S Pleasant Valley Rd, 22601
Vision & Vino: A Vision Board Social - TICKET NEEDED
Fri, 23 Jan at 06:00 pm
2 N Kent St, Winchester, VA 22601-5038, United States
Santa Express
Sat, 13 Dec at 12:00 pm
231 E Piccadilly St, Winchester, VA, 22601
Christmas Dinner and The Dixie Moon Band
Sat, 20 Dec at 04:30 pm
1730 Berryville Pike, Winchester, VA
BOOM! Is back at the backseat
Fri, 16 Jan at 08:00 pm
Backseat Bar and Grill
Cold Beer & Common Sense with Spencer Hatcher
Fri, 12 Dec at 08:00 pm
114 Full House Drive , Winchester, VA, United States, Virginia 22603
Emo Night Karaoke 1/23 @ Bright Box Theater
Fri, 23 Jan at 08:00 pm
Bright Box Theater
USD 21
COCOA AND COOKIES WITH SANTA
Sat, 13 Dec at 01:00 pm
T-Bone's Bar & Grill
A DIVA's Christmas Special
Sat, 20 Dec at 05:30 pm
Bright Box (Winchester, VA)
Wait Until Dark
Thu, 15 Jan at 07:00 pm
Winchester Little Theatre
Backseat Winchester Va
Sat, 20 Dec at 08:00 pm
Backseat Bar and Grill
Light the World
Fri, 12 Dec at 06:00 pm
399 Apple Pie Ridge Rd, Winchester, VA, United States, Virginia 22603
Santa Brunch @ Vibrissa Beer
Sun, 14 Dec at 10:00 am
Vibrissa Beer (Winchester, VA)
Trans Family Affinity Group
Thu, 11 Dec at 06:00 pm
124 W Piccadilly St, Winchester, VA 22601-3916, United States
2025 Winchester Wreaths Across America Day - Wreath Laying and Ceremony
Sat, 13 Dec at 11:00 am
401 National Ave, Winchester, VA, United States, Virginia 22602
Fierce Love Rescue at Skyline Harley-Davidson | It's a Paw-liday Extravaganza!
Sat, 13 Dec at 10:00 am
Skyline Harley-Davidson
Someone Special Dance
Sat, 07 Feb at 06:00 pm
West Oaks Farm Market
A Christmas Carol
Sun, 14 Dec at 03:00 pm
Grace Evangelical Lutheran Church 26 W Boscawen St A-201, Winchester, VA 22601
Fork In The Road @ Winchester Eagles!
Sat, 13 Dec at 07:00 pm
Winchester Virginia Eagles Club 824
Shark Pit 7-Year Anniversary Seminar
Sun, 04 Jan at 12:00 pm
210 Fort Collier Road, Unit 6, Winchester, VA
Winchester Moose Lodge 1283
Fri, 23 Jan at 07:00 pm
Winchester Moose Family Center 1283
Christmas Music Bingo
Wed, 17 Dec at 06:30 pm
4305 Middle Road, Winchester, VA, United States, Virginia 22602
Collin Raye in Winchester
Sat, 17 Jan at 08:00 pm
Backseat Events
Flute Ensemble
Sat, 13 Dec at 07:30 pm
Goodson Chapel Recital Hall
The Nutcracker Ballet
Sat, 13 Dec at 02:00 pm
John Handley High School
Go Big and Stay Home
Sat, 13 Dec at 04:15 pm
Patti's Place
USD 87
LAST CALL HOLIDAY BAZAAR
Sat, 20 Dec at 08:00 am
164 Poorhouse Rd, Winchester, VA
Chamber Brass Recital
Mon, 15 Dec at 07:30 pm
Goodson Chapel Recital Hall
Wait Until Dark at Winchester Little Theatre Inc.
Sat, 17 Jan
Winchester Little Theatre Inc.
The Amish Outlaws Return to Backseat Events in Winchester, VA
Sat, 10 Jan at 08:00 pm
114 Full House Drive , Winchester, VA, United States, Virginia 22603
Winchester Elks Lodge - Tuff Luck Band
Sat, 27 Dec at 07:00 pm
Fraternal Order of Elks Lodge 867
Ugly Sweater Contest & Thieves Christmas!
Sat, 13 Dec at 06:00 pm
1730 Berryville Pike, Winchester, VA
The Bass Club Presents: MAD DUBZ
Fri, 12 Dec at 08:00 pm
Bright Box Theater
USD 13 to 29
FLW LIVE at Piccadillys!
Fri, 19 Dec at 07:30 pm
Piccadilly's Public House and Restaurant
Dec 2025 Holiday Tour & Hannukah event at Peaceful Fields Sanctuary
Sun, 21 Dec at 02:00 pm
Peaceful Fields Sanctuary
USD 13
Women's Qigong
Mon, 15 Dec at 05:30 pm
301 N Cameron St, Winchester, VA 22601-4899, United States
Teen Art Club
Thu, 11 Dec at 04:30 pm
Museum of the Shenandoah Valley
Winchester Elks
Fri, 06 Feb at 07:00 pm
466 Front Royal Pike, Winchester, VA 22602-7315, United States
Matriarchs of Midwifery: Wisdom, Care & Legacy
Fri, 17 Apr at 05:00 pm
School of Business - Shenandoah University
Chuggalug at our fav Winchester Elks!
Sat, 03 Jan at 07:00 pm
Fraternal Order of Elks Lodge 867
Young Adult Affinity Group
Tue, 16 Dec at 06:00 pm
124 W Piccadilly St, Winchester, VA 22601-3916, United States
2026 Legislative Preview
Sat, 10 Jan at 09:30 am
Greenwood Mill Elementary School
Cash Party
Sat, 24 Jan at 05:00 pm
250 Costello Dr, Winchester, VA 22602-4310, United States
The Santa's Express Old Town Cookie Crawl
Sat, 13 Dec at 12:00 pm
Old Town Winchester Walking Mall
Heir and a Parent: Christmas Cookie House
Sat, 13 Dec at 01:00 pm
27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
Winter Disco Drag Show
Sat, 10 Jan at 08:00 pm
Winchester Brew Works
USD 18
Legacy Christian Academy Christmas Concert
Tue, 16 Dec at 06:30 pm
Daniel Morgan Middle School
Free
Christmas Vacation Watch Party
Tue, 23 Dec at 07:00 pm
14 W Boscawen St, Winchester, VA, United States, Virginia 22601
Joe Nichols
Wed, 28 Jan at 07:00 pm
Backseat Events
Literacy Family Holiday Party with Santa
Sat, 13 Dec at 02:00 pm
Winchester Public Schools
Gourmet Cookies
Sat, 13 Dec at 10:00 am
27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
Fire Pit Fridays
Fri, 19 Dec at 04:00 pm
4063 Middle Rd, Winchester, VA, United States, Virginia 22602
Jackyl in Winchester
Fri, 30 Jan at 08:00 pm
Backseat Events
December Friday² Free BEER & WINE Tasting + Pop Up Market
Fri, 12 Dec at 05:00 pm
90 Featherbed Ln, Winchester, VA
The Red Gobbo Secret Gift Exchange
Sat, 13 Dec at 11:00 am
255 Market Street, Winchester, VA, United States, Virginia 22603
University of Scouting
Sat, 17 Jan at 08:00 am
James Wood High School
Guest Reading: Miss Elizabeth’s Tarot
Sat, 13 Dec at 11:00 am
125 S. Loudoun Street, Winchester, VA
NW Works Chimers
Sat, 13 Dec at 02:30 pm
Armstrong Concert Hall
Old Town Winchester New Year's Eve Celebration 2026
Wed, 31 Dec at 06:00 pm
Old Town, Winchester
Candlelight Christmas Experience
Tue, 23 Dec at 07:00 pm
2870 Middle Rd, 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
2025-2026 Winter Series #3 - Wags at West Oaks Farmers Market
Sat, 03 Jan at 09:30 am
West Oaks Farm Market
The Philadelphia Eagles vs the Buffalo Bills: Live at The Cider House
Sun, 28 Dec at 04:25 pm
30 East Piccadilly Street, Winchester, VA, United States, Virginia 22601
Backseat Events - Joe Nichols - Mack Berry Band
Thu, 29 Jan at 08:00 pm
Backseat Events
Wee One's Wednesdays
Wed, 17 Dec at 09:00 am
1001 E Cork St, Winchester, VA, United States, Virginia 22601
14th Annual Beer & Carols Celebration
Sun, 21 Dec at 06:00 pm
Piccadilly's Public House and Restaurant
🎁 2nd Annual Kids Shopping Free Event at SPCA Thrift! 🎄
Fri, 19 Dec at 12:00 pm
1944 Abrams Creek, Winchester, VA, United States, Virginia 22601
Standup Comedy at Escutcheon Brewing! (Winchester, Va)
Fri, 14 Nov at 08:00 pm
Escutcheon Brewing Co.
USD 13
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Upcoming Winchester Events