• 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 business connections, offering relatable and humorous life lessons. Come meet Renee, sip some wine, and grab a signed copy of her book!

  • 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

    šŸ« 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 […]

    $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

    šŸ’˜ Calling all besties! You’re officially invited to Galentine’s Night šŸ’˜ 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 […]

  • Spin to Win-chester

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

    Spin to Win-Chester šŸš“ā€ā™‚ļøšŸ”„ 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. […]

    $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 […]

  • Author Event: James Blakey – Shenandoah Fantastic

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

    Get the latest from local author James Blakey, SHENANDOAH FANTASTIC, and experience the Valley like never before! Time travelers at the Shakespeare Center…Space aliens at Route 11 Potato Chips…Trolls beneath […]