Winchester Arts Events

Farm & Maker’s Saturday Market

2502 N. Frederick Pike, Winchester, VA 25 Oct 2025

Blocktober

Museum of the Shenandoah Valley 26 Oct 2025

Model Train Show and Sale

Winchester Moose Lodge, 215 E Cork Street, Winchester, VA 8 Nov 2025

Wellington 101

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 7 Nov 2025

Poetry and Tarot for Creative Practice

125 S. Loudoun Street, Winchester, VA 25 Oct 2025

A Christmas Carol

Winchester Little Theatre 6 Nov 2025

Pierogis!!

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 25 Oct 2025

Austin Meade + Elvie Shane Co-Headline

186 North Loudoun Street, Winchester, VA 8 Nov 2025

Standup Comedy at Escutcheon Brewing!

Escutcheon Brewing Co. 14 Nov 2025

EQUIP - Empowering the Next Generation with Dr. Jeff Myers

3217 Middle Rd, Winchester, VA 22602-5108, United States 30 Oct 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 16 Nov 2025

Gallery Explorers: Winter Landscape Holiday Cards

901 Amherst St, Winchester, VA, United States, Virginia 22601 20 Dec 2025

Drum Fever Workshop

28 W Hart Street, Winchester, VA, United States, Virginia 22601 2 Nov 2025

German I

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 1 Nov 2025

HalloWinchester Pub Crawl

14 W Boscawen St 25 Oct 2025

Breaking Breads

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 15 Nov 2025

Winter Wonderland Christmas Market

Millwood Station Banquet Hall 22 Nov 2025

Bright Box Halloween Party ft. Dj Ophie + Special Guest Dj Curfew

Bright Box Theater 31 Oct 2025

Gallery Explorers: Winter Landscape Holiday Cards

901 Amherst St, Winchester, VA, United States, Virginia 22601 15 Nov 2025

Cumberland Road at Bright Box Theater!

Bright Box Theater 27 Dec 2025

Bingo For The Animals

2077 N Frederick Pike 15 Nov 2025

Better Human Book Club

100 W Piccadilly St, Winchester, VA, United States, Virginia 22601 5 Nov 2025

A Christmas Carol at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 7 Nov 2025

8th Annual Veteran's Day Benefit

1300 Senseny Rd, Winchester, VA 22602-6418, United States 7 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 15 Nov 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 22 Nov 2025

Four Color Fright Fest 2025!

80 Weems Ln, Winchester, VA, United States, Virginia 22601 25 Oct 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 29 Nov 2025

Wait Until Dark

Winchester Little Theatre 16 Jan 2026

Asian Dumplings

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 8 Nov 2025

Decision Height at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 13 Mar 2026

Holistic Healing Workshop Series Winchester, VA

Winchester Country Club 15 Nov 2025

Pierogis!!

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 7 Dec 2025

WLT - Fundraiser - A Christmas Carol

315 W Boscawen St, Winchester, VA 22601-3809, United States 6 Nov 2025

Exploring da Vinci in Winchester, VA

Grace Evangelical Lutheran Church 26 Boscawen St Winchester, VA 22601 26 Oct 2025

The Art Remedy: A Mindfulness Painting Workshop

901 Amherst St, Winchester, VA, United States, Virginia 22601 15 Nov 2025

Adult Poetry Workshop: Exploring Ability & Identity

901 Amherst St, Winchester, VA, United States, Virginia 22601 31 Oct 2025

Elijah - Artist

The Monument - VA 20 Nov 2025

A Day in the Kitchen: Advanced Macaron

27 North Loudoun Street, Winchester, VA, United States, Virginia 22601 20 Dec 2025

Phelpsmore Farm Stone Soup Gathering

303 Phelpsmore Ln, Winchester, VA 22602-2074, United States 6 Nov 2025

Meet the Artist: Lisa Elmaleh

901 Amherst St, Winchester, VA, United States, Virginia 22601 12 Nov 2025

Dancing Thru the Decades

Backseat Events 7 Feb 2026

Wait Until Dark at Winchester Little Theatre Inc.

Winchester Little Theatre Inc. 17 Jan 2026

Keith Harkin Trio - Winchester VA Bright Box Theater

Bright Box Theater 9 Dec 2025

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 23 Nov 2025

Little Noon Music - Shenandoah Conservatory's Trombone Collective

100 W Piccadilly St, Winchester, VA, United States, Virginia 22601 5 Dec 2025

Gallery Explorers: Winter Landscape Holiday Cards

901 Amherst St, Winchester, VA, United States, Virginia 22601 16 Dec 2025

Paws & Purrs: Howl-O-Wine at the Vineyard, a Fundraiser for Blue Ridge Care

James Charles Winery & Vineyard 29 Oct 2025

Teen Art Club: Holiday Crafts

901 Amherst St, Winchester, VA, United States, Virginia 22601 11 Dec 2025

Decision Height

Winchester Little Theatre 12 Mar 2026

A Christmas Carol at Winchester Little Theatre

Winchester Little Theatre 13 Nov 2025

First Night Winchester at the MSV

901 Amherst St, Winchester, VA, United States, Virginia 22601 31 Dec 2025

Parking A Christmas Carol

Winchester Little Theatre Inc. 16 Nov 2025

A Christmas Carol

Winchester Little Theatre Inc. 16 Nov 2025

Record Store Day Black Friday 2025

48 South Loudoun St., Winchester, VA, United States, Virginia 22601 28 Nov 2025

Youth Workshop: Ceramic Decorative Arts

901 Amherst St, Winchester, VA, United States, Virginia 22601 1 Nov 2025

Virginia Gourd Show & Sale

901 Amherst St, Winchester, VA, United States, Virginia 22601 8 Nov 2025

Gallery Talk: Frida Kahlo

901 Amherst St, Winchester, VA, United States, Virginia 22601 14 Nov 2025

Art Ability: Frida Kahlo

901 Amherst St, Winchester, VA, United States, Virginia 22601 6 Nov 2025

Teen Art Club: Art in the Halls

901 Amherst St, Winchester, VA, United States, Virginia 22601 13 Nov 2025

Winchester Audio Tour: Echoes of Legends and Landmarks

Beth El Congregation (Winchester, Virginia) 27 Sep 2025

Homeschool Wednesday Workshop: Fall Plein Air Painting

901 Amherst St, Winchester, VA, United States, Virginia 22601 5 Nov 2025

Awesome Scavenger Hunt - Winchester Wonders

12 N Cameron St 19 Nov 2024