• Old Town on the Rocks

    Loudoun Street Pedestrian Mall

    Old Town on the Rocks January 16โ€“18, 2026 | Old Town Winchester Old Town on the Rocks is a weekend-long bourbon and cocktail competition celebrating the creativity of Old Town […]

    Free
  • Author Event: Heidi Christopher – Lies the Dirt Keeps

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

    She came home searching for her sister. What she uncovered could destroy them all. Johnna LaGrange photographs death for a living. But when she gets the call that her younger […]

    Free
  • FREE Midday at The YDC!

    FREE Midday at The YDC!

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

    Midday at The YDC is a relaxed, inclusive daytime program designed to give families a place to connect, learn, and spend meaningful time together. Open to all school-aged children and […]

    Free
  • 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
  • BrandFest

    The HIVE at Shenandoah University, Winchester, VA 1460 University Drive, Winchester, V, United States

    Looking for a marketing edge to boost sales and profits? Join us for the inaugural BrandFest and gain practical tips, tools, and resources to strengthen your local brand. Learn from […]

    Free
  • Galentine’s Night Out

    Galentine’s Night Out

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

    Join us for a fun and fabulous Galentineโ€™s Night Out at The YDC! Enjoy a guided painting experience, light bites, and a glass of something sweet as you celebrate friendship […]

    $45
  • Spin to Win-chester

    Valley Health Fitness Center 401 Campus Blvd, Winchester, V, United States

    Spin to Win-Chester ๐Ÿšดโ€โ™‚๏ธ๐Ÿ”ฅ Think youโ€™ve got what it takes? Spin to Win-Chester is a high-energy spin-a-thon where riders compete, fundraise, and push themselvesโ€”all in support of Old Town Winchester. […]

    $250
  • FREE Midday at The YDC!

    FREE Midday at The YDC!

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

    Midday at The YDC is a relaxed, inclusive daytime program designed to give families a place to connect, learn, and spend meaningful time together. Open to all school-aged children and […]

    Free
  • 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
  • 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
  • FREE Midday at The YDC!

    FREE Midday at The YDC!

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

    Midday at The YDC is a relaxed, inclusive daytime program designed to give families a place to connect, learn, and spend meaningful time together. Open to all school-aged children and […]

    Free
  • FREE Midday at The YDC!

    FREE Midday at The YDC!

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

    Midday at The YDC is a relaxed, inclusive daytime program designed to give families a place to connect, learn, and spend meaningful time together. Open to all school-aged children and […]

    Free