• 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 — for the person and their loved ones. That’s why at Bridging the Gaps, we’re offering 𝐅𝐢𝐫𝐬𝐭 𝐖𝐞𝐝𝐧𝐞𝐬𝐝𝐚𝐲 𝐂𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐲 𝐀𝐝𝐝𝐢𝐜𝐭𝐢𝐨𝐧 𝐈𝐧𝐟𝐨𝐫𝐦𝐚𝐭𝐢𝐨𝐧 𝐍𝐢𝐠𝐡𝐭, a 𝐟𝐫𝐞𝐞 𝐦𝐨𝐧𝐭𝐡𝐥𝐲 𝐞𝐯𝐞𝐧𝐭 […]

    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
  • Author Event: Renee Ventrice – Pour Relationship Choices

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

    Pour Relationship Choices: Every Sip Tells a Story Beyond the Glass! by Renee Ventrice is a wine-themed memoir that uses wine pairings to explore personal relationship stories, from romantic to […]

  • Author Event: Elmdea Adams – Moving Forward

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

    Moving Forward is an evocative memoir by Elmdea Adams, capturing the poignant journey of a caregiver navigating the final year of her husband John’s life, as well as her own […]

  • Chocolate Escape

    Loudoun Street Pedestrian Mall

    🍫 Chocolate Escape is coming to Old Town Winchester on Saturday, February 7th! Treat yourself (and your friends) to a sweet stroll through downtown with chocolates, treats, and fun surprises […]

    Free
  • Hugs & Dishes Sale

    Kimberly's 135 N Braddock St, Winchester, VA, United States

    Everything tabletop, dishes, and jewelry on sale at 20% off - perfect timing for your Valentine's Day Date & Dinner. Exclusively, this sale includes ALL special orders!

  • Celebrating Black History Month: Rhythm & Roots Night

    Bistro SOJO 12 S. Braddock Street, Winchester, VA, United States

    Rhythm & Roots Night A Black History Month Celebration in Old Town Join us for an evening of music, culture, and community as we celebrate Black History Month with Rhythm […]

    $35
  • 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 Galentine’s Night Out at The YDC! Enjoy a guided painting experience, light bites, and a glass of something sweet as you celebrate friendship […]

    $45
  • Galentines Night @ Vibrissa- Winchester

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

    💘 Calling all besties! You’re officially invited to Galentine’s Night 💘 Grab your girls and join us for a night full of love, laughs, and all the vibes: -Flower Bar -Permanent Jewelry -Custom Hat Bar -Photo Booth -DJ -Drink Specials Date: Thursday, February 12th, 2026 Time: 6:00–9:00 PM Location: 10 N Kent Street, Winchester, VA […]

    Free
  • Celebrating Black History Month: Art & Spoken Word Night

    The Typewriter Studio 127 S. Braddock Street, Winchester, VA, United States

    Join us for an evening of creativity, expression, and community at Art & Spoken Word Night at Typewriter Studio. As part of Black History Month in Old Town, this event will spotlight local artists, poets, and performers sharing work that reflects culture, history, identity, and lived experience. From powerful spoken word to visual art and […]

    Free
  • Author Event: Rich Follett – The Day it Rained Popcorn

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

    Welcome to Bliss, a sunny little village where gold is everywhere, but no one really needs it. Life is peaceful until a greedy dragon arrives and starts taking every golden thing in sight. The villagers are scared, the knights are trying their best, and hope is fading fast. Then two tiny children with a very […]