🍫 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 […]
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!
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 […]
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 […]
💘 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 […]
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 […]
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 🚴♂️🔥 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: […]
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 […]
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 Luray Caverns… Twenty-four stories of fantasy, horror, and science fiction in all.
Join us for a meaningful and memorable evening as we celebrate Black History Month with History & Cocktails Night at Bright Box Theater. This relaxed, intimate event will feature short talks and local storytellers sharing stories that highlight Black history in Winchester and the surrounding region. It’s a chance to connect with our community’s past […]
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 their caregivers, this drop-in experience invites families to use The YDC as a community space that supports curiosity, creativity, and connection. During Midday at The […]