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  • 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! ๐Ÿป๐Ÿ›๏ธBeer & shopping?! who knew those were such a good […]

    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 […]

  • Catalyst Quartet

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

    Shenandoah New Music Hailed by The New York Times as โ€œinvariably energetic and finely burnished,โ€ the Grammy Award-winning Catalyst Quartet is redefining the classical music experience. Founded by the internationally […]

    $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 […]

    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 […]

    Free

  • Trunk or Treat on Loudoun Street

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

    ๐ŸŽƒ Trunk or Treat on Loudoun Street ๐Ÿ“… Saturday, October 18, 2025 ๐Ÿ•“ 4:00 โ€“ 7:00 PM ๐Ÿ“ 302 S. Loudoun Street, Winchester, VA (YDC Parking Lot) FREE & open […]

    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

    Winchesterโ€™s biggest Halloween street party is back! Live music, alien vibes, $500 in costume prizes + raffle gift basket โ€” all benefiting Katieโ€™s Comfort House.

    $10

  • Halloween Costume Dance Party

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

    Join us Friday October 31st from 8pm until close for a night of thrilling dance moves & spooky Halloween costumes! DJ Chris Jarrell, photobooth, costume contest, drink & food Specials, […]

    free

  • Author Event: Dale Watten – Dream Valley Shenandoah

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

    Local author Dale Watten has a new book that showcases the native and naturalized flowers of the Shenandoah Valley in Western Virginia. Written in verse, it is accompanied by beautiful […]

  • First Wednesday Community Information Night

    First Wednesday Community Information Night
    Bridging the Gaps 31 S. Braddock Street, Winchester, V, United States

    Addiction is a struggle โ€” for the person and their loved ones. Thatโ€™s why at Bridging the Gaps, weโ€™re offering ๐…๐ข๐ซ๐ฌ๐ญ ๐–๐ž๐๐ง๐ž๐ฌ๐๐š๐ฒ ๐‚๐จ๐ฆ๐ฆ๐ฎ๐ง๐ข๐ญ๐ฒ ๐€๐๐๐ข๐œ๐ญ๐ข๐จ๐ง ๐ˆ๐ง๐Ÿ๐จ๐ซ๐ฆ๐š๐ญ๐ข๐จ๐ง ๐๐ข๐ ๐ก๐ญ, a ๐Ÿ๐ซ๐ž๐ž ๐ฆ๐จ๐ง๐ญ๐ก๐ฅ๐ฒ ๐ž๐ฏ๐ž๐ง๐ญ […]

    Free

  • Cheesin’ for a Reason – a grilled cheese & tomato soup extravaganza

    Winchester Walking Mall Loudoun Street, Winchester, V, United States

    Our 1st Annual Grilled Cheese and Tomato Soup Extravaganza for Winchester! ๐Ÿง€๐Ÿ… WATTS will be "Cheesin' for a Reason" this fall and we hope you'll come out and join us […]

    $10 โ€“ $20