Events

🍫 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 […]

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 […]

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 […]

💘 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 […]

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 […]

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 […]

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 […]

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 […]

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 […]

The Fort Loudoun DAR chapter is sponsoring an event akin to "Where's Waldo" where participants get a Passport and go to the 38 participating merchants in Old Town to locate each Rev War Hero. Once they get 10 they can go to the Winchester Frederick Co. Visitor Center for a prize.