Banned Books Week

Winchester Book Gallery 7 North Loudoun Street, Winchester, V, United States

The American Library Association and Banned Books Week Coalition are pleased to announce the theme for Banned Books Week 2025: “Censorship Is So 1984. Read for Your Rights.” Banned Books Week will take place October 5 – 11, 2025. As always, we will be celebrating Banned Books Week with a huge table of banned books […]

Free
The Magic Flute ballet

The Magic Flute ballet

Vostrikov's Academy of Ballet 20 West Cork Street, Winchester, V, United States

Virginia Youth Ballet presents a classic ballet, The Magic Flute. Let the Magic of Kindness and Love Enchant You Step into a world where music holds the power to change destinies and love conquers all obstacles. In a charming village shadowed by struggle and longing, a humble boy’s act of generosity awakens the magic of a […]

$12

Savor the World

Godfrey Miller Center 28 South Loudoun Street, Winchester, V, United States

A memorable evening of fine wine, connection, and culinary delight—all in support of a meaningful cause. Explore international wine and food pairings in a progressive tasting experience. The night culminates with a lively Wine Pull, where every ticket gets a bottle of wine.

$125

Beer and Halloween Candy Pairing at Murphy Beverage Company

Murphy Beverage Company 167 N Loudoun Street, Winchester, V, United States

We'll be pouring samples of beer paired with candy to help you get ready for Halloween. Sponsored by Taryn Obssuth, realtor at Keller Williams, and Kate A. Walker of Integrity Home Mortgage.

Free

Fall Vendor Pop-Up Market

Vibrissa Beer 10 N. Kent St, WINCHESTER, V, United States

Join us Sunday, October 12th from 1-3pm, rain or shine, to support some local small business at your hometown brewery! 🍻🛍️Beer & shopping?! who knew those were such a good idea together!!! Vendors: Cici's Permanent Jewelry Bar Lost in the Stitch Southern Belle Creations Sipsy's T's Glitter & Grace Country & the Geek Creations of […]

Free

Tech-Forward Town: Digital Tools for a Connected Community

Winchester Brew Works

We love hearing from our amazing Old Town community! That's why Friends of Old Town is hosting monthly outreach and input sessions all year long. These laid-back, open-forum meetups are a great chance to share ideas, chat about what's happening in Old Town, and help shape our future together. Each session focuses on a fun, […]

Catalyst Quartet

Bright Box 15 N Loudoun Street, Winchester, VA, United States

Shenandoah New Music Hailed by The New York Times as “invariably energetic and finely burnished,” the Grammy Award-winning Catalyst Quartet is redefining the classical music experience. Founded by the internationally acclaimed Sphinx Organization, the ensemble is driven by a belief in the unifying power of music and a passion for collaboration, innovation and inclusion. Their […]

$18
Shake Your Booty 70s Dance Night

Shake Your Booty 70s Dance Night

Vibrissa Beer 10 N. Kent St, WINCHESTER, V, United States

70s BABY!!! 70s music and beyond, 70s attire encouraged but not required. Come for Community, Dinner and Drinks -- Stay to DANCE! (or just come to dance!) Bring your friends and come Shake Your Booty with us!

Free
Shake Your Booty 70s Dance Night

Shake Your Booty 70s Dance Night

Vibrissa Beer 10 N. Kent St, WINCHESTER, V, United States

70s BABY!!! 70s music and beyond, 70s attire encouraged but not required. Come for Community, Dinner and Drinks -- Stay to DANCE! (or just come to dance!) Bring your friends and come Shake Your Booty with us!

Free

Trunk or Treat on Loudoun Street

Youth Development Center 302 S Loudoun Street, Winchester, V, United States

🎃 Trunk or Treat on Loudoun Street 📅 Saturday, October 18, 2025 🕓 4:00 – 7:00 PM 📍 302 S. Loudoun Street, Winchester, VA (YDC Parking Lot) FREE & open to all - thanks to our generous YDC donors! 👻 Join us for a spook-tacular evening of safe, family-friendly Halloween fun right in the heart of […]

Free

HalloWinchester Old Town Merchant Trick r Treat

Loudoun Street Pedestrian Mall

Bring the family to Old Town Winchester for a safe and festive afternoon of trick-or-treating! Local merchants along the Loudoun Street Pedestrian Mall will be handing out candy and goodies to children in costume. Stroll through downtown, show off your Halloween spirit, and enjoy the seasonal decorations, shops, and restaurants that make Old Town such […]

Free

HalloWinchester Pub Crawl

Loudoun Street Pedestrian Mall

Winchester’s biggest Halloween street party is back! Live music, alien vibes, $500 in costume prizes + raffle gift basket — all benefiting Katie’s Comfort House.

$10