#StayHappening

Upcoming Winchester Events

Check out what's happening all around Winchester, VA

100 upcoming events Winchester, United States Updated 6 Nov 2026

All 100 events in Winchester

251st USMC Ball

Sat, 14 Nov at 06:00 pm 4063 Middle Rd, Winchester, VA, United States, Virginia 22602
NONPROFIT

Plaid Friday

Fri, 27 Nov at 08:00 am Old Town Winchester Walking Mall

The Nighthawks!

Sat, 28 Nov at 08:00 pm Bright Box (Winchester, VA)
MUSIC

Evening With The Babys

Thu, 31 Dec at 08:30 pm The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA
USD 162 FITNESS

JWHS CTE Career Fair

Thu, 19 Nov at 07:30 am 161 Apple Pie Ridge Road, Winchester, VA, United States, Virginia 22603

Sapphic Trivia Night

Sat, 14 Nov at 06:00 pm 124 W. Piccadilly Street, Winchester, VA, United States, Virginia 22601
SPORTS

Pictures with Santa

Sat, 19 Dec at 10:00 am 1597 Senseny Rd, Winchester, VA
PICTURES-WITH-SANTA

Bryan Stuzman

Fri, 06 Nov at 07:30 pm 125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601
MUSIC

New York Style Bagel Class

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

Barker & Schuster

Fri, 20 Nov at 07:30 pm 125 E Piccadilly Street, Winchester, VA, United States, Virginia 22601
MUSIC

Puff the Magic Pastry

Sat, 07 Nov at 10:00 am 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
WORKSHOPS

Open House

Sat, 07 Nov at 12:00 pm 2654 Valley Ave, Suite A, Winchester, VA, United States, Virginia 22601
HEALTH-WELLNESS

Sounds of the Season

Sat, 21 Nov at 07:00 pm 205 W Piccadilly St, Winchester, VA 22601-3906, United States

Clay Gingerbread House

Sun, 15 Nov at 11:00 am 157 N Loudoun St, Winchester, VA, United States, Virginia 22601
CHRISTMAS

MJT

Thu, 19 Nov at 08:00 pm Bright Box Theater
MUSIC

Knife Skills Class

Sat, 21 Nov at 01:00 pm 27 North Loudoun Street, Winchester, VA, United States, Virginia 22601
WORKSHOPS

Lineage Society Workshops

Thu, 12 Nov at 10:30 am 100 W Piccadilly St, Winchester, VA, United States, Virginia 22601
WORKSHOPS

Sounds of the Season

Sun, 22 Nov at 03:00 pm 116 S Loudoun St, Winchester, VA 22601-4722, United States
CHRISTMAS