• 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 experts in the Winchester community (and beyond) in three focused sessions: • Building a Local Brand • Social Media that Sells • Customers as Advocates […]

    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 path through grief. Through a tapestry of journal entries, social media posts, and personal reflections, the narrative offers an unfiltered glimpse into the harsh realities […]

  • 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 at participating Old Town businesses all day long. It’s the perfect excuse to shop local and enjoy a little winter fun in Old Town. A […]

    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 & Roots Night at Bistro SOJO. This special gathering will honor the rich musical legacy and cultural influence of Black artists through an atmosphere filled […]

    $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 and creativity in the heart of downtown Winchester. Whether you come solo or with your favorite gals, you’ll leave with your own masterpiece and memories […]

    $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 […]

  • Spin to Win-chester

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

    Spin to Win-Chester 🚴‍♂️🔥 Think you’ve got what it takes? Spin to Win-Chester is a high-energy spin-a-thon where riders compete, fundraise, and push themselves—all in support of Old Town Winchester. Join us Saturday, February 21 at Valley Health Wellness & Fitness Center for a Winchester-themed ride led by Pam Lambert. Choose Your Challenge Beginner Ride: […]

    $250
  • Author Event: Greg Kujala – Working at Love

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

    Working at Love continues the story of Amanda and David following their graduation from Jefferson Medical College. Amanda chose a residency in pathology at Jefferson, while David opted for psychiatry at the Brigham in Boston. Their long-distance connection over the course of the next five years was difficult to maintain. Both Amanda and David grew […]