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  • 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 […]

    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 […]

    $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 […]

    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