W.O.W. - September Networking Event Tue 8 Sep 2026, 11:00 AM — Meetup The George Washington A Wyndham Grand Hotel · 103 East Piccadilly Street, Winchester, VA 22601
Winchester Hygiene Night - The Hidden Implant Patient Thu 10 Sep 2026, 5:30 PM — class Winchester Country Club · 1300 Senseny Road, Winchester, VA 22602
Come From Away — Selah Theatre Project Fri 11 Sep 2026, 7:00 PM — Theater 302 N Braddock St · 302 N Braddock St, Winchester, VA 22601
Standup Comedy at Escutcheon Brewing Fri 11 Sep 2026, 8:00 PM — Comedy Escutcheon Brewing Co. · 142 W Commercial St, Winchester, VA 22601 · 21+
Sunflower Festival 2026 Sat 12 Sep 2026, 10:00 AM — Live music The Homestead Farm at Fruit Hill Orchard and Sugar Shack LLC · 2502 North Frederick Pike, Winchester, VA 22603
Dancing with the Goats at Peaceful Fields Sanctuary! Sat 12 Sep 2026, 3:00 PM — Meetup Peaceful Fields Sanctuary · 153 Peacefield, Winchester, VA 22603
Sevendust Tribute Show, feat. Illusion & Sonic Disciple @Backseat Events Sat 12 Sep 2026, 7:00 PM — Live music Backseat Events USA · 114 Full House Drive, Winchester, VA 22603
Meet the Bees & Beekeepers Sun 13 Sep 2026, 2:00 PM — Meetup Museum of the Shenandoah Valley · 901 Amherst St, Winchester, VA 22601 · Registration required
Lebanese Wine Pairing Dinner at Byblos Winchester Sun 13 Sep 2026, 6:00 PM — Meetup Byblos Winchester · 3111 Valley Ave #108 Creekside Station, Winchester, VA 22601
Bridging The Gap : Episodes 3+4 Premiere Sun 13 Sep 2026, 7:00 PM — Meetup The Wine Room at Taylor Pavilion · 120 North Indian Alley, Winchester, VA 22601
MSV at Night: Amy Andrews Fri 18 Sep 2026, 5:00 PM — Live music Museum of the Shenandoah Valley · 901 Amherst St, Winchester, VA 22601 · Discounted evening ticket
South African Wine and Food Festival Sat 19 Sep 2026, 12:00 PM — Festival Patti's Place · 3178 Laurel Grove Road, Winchester, VA 22602 · 21+
Sept Guided Tour of Peaceful Fields Sanctuary Sun 20 Sep 2026, 2:00 PM — Meetup Peaceful Fields Sanctuary · 153 Peacefield, Winchester, VA 22603
Community Connect and Serve Thu 24 Sep 2026, 12:00 AM — Meetup The Church of Jesus Christ of Latter-day Saints · 399 Apple Pie Ridge Road, Winchester, VA 22603
Boost Your Project Management Techniques Training in Winchester, VA Fri 25 Sep 2026, 9:00 AM — class Regus · Regus, Winchester, VA 22601
Pappy’s Cards and Collectables Card Show Sat 26 Sep 2026, 9:00 AM — Meetup Millbrook High School · 251 First Woods Drive, Winchester, VA 22603
Delivery | Winchester Wed 30 Sep 2026, 11:00 AM — class Handley Regional Library Auditorium · 100 West Piccadilly Street, Winchester, VA 22601
Oktoberfest at The Exchange on Loudoun Fri 2 Oct 2026, 5:00 PM — Live music The Exchange on Loudoun · 186 North Loudoun Street, Winchester, VA 22601
PRIDE at the MSV Sat 3 Oct 2026, 10:00 AM — Pride Museum of the Shenandoah Valley · 901 Amherst St, Winchester, VA 22601 · Free site-wide admission
Experience fusion KARAOKE Sat 3 Oct 2026, 5:00 PM — Karaoke 1169 Berryville Ave · 1169 Berryville Avenue, Winchester, VA 22601
A Night of Elvis: 50's through the 70's Sat 3 Oct 2026, 7:00 PM — Live music Backseat Events USA · 114 Full House Drive, Winchester, VA 22603
FemininiTea Tue 6 Oct 2026, 11:00 AM — Meetup The George Washington A Wyndham Grand Hotel, 103 East Piccadilly Street, Winchester, VA, USA · 103 East Piccadilly Street, Winchester, VA 22601
LAPTOP EVENT FOR VETERANS 10/16/26 Fri 16 Oct 2026, 9:00 AM — Meetup HIVE — Hub for Innovators, Veterans and Entrepreneurs · 608 Millwood Avenue, Winchester, VA 22601
Celebrate Community Cats this Fall in Style Sun 18 Oct 2026, 2:00 PM — Meetup The George Washington A Wyndham Grand Hotel · 103 East Piccadilly Street, Winchester, VA 22601
Boost Your Project Management Techniques Training in Winchester, VA Fri 23 Oct 2026, 9:00 AM — class Regus · Regus, Winchester, VA 22601
Experience fusion KARAOKE Sat 7 Nov 2026, 5:00 PM — Karaoke 1169 Berryville Ave · 1169 Berryville Avenue, Winchester, VA 22601
Emo Night Karaoke Sat 7 Nov 2026, 7:00 PM — Karaoke Bright Box Theater · 15 N Loudoun St, Winchester, VA 22601 · 21+
Boost Your Project Management Techniques Training in Winchester, VA Fri 27 Nov 2026, 9:00 AM — class Regus · Regus, Winchester, VA 22601
Winchester, Frederick, Clarke Republican Women Christmas Lunch Wed 9 Dec 2026, 11:30 AM — Meetup Village Square Restaurant · 103 North Loudoun Street, Winchester, VA 22601
Evening With The Babys Thu 31 Dec 2026, 8:30 PM — Live music The George Washington, A Wyndham Grand Hotel · 103 E Piccadilly St, Winchester, VA 22601 · 21+
Listings are seeded from venue and organiser calendars. See them on the map.