Friends of Old Town celebrates and enhances Old Town Winchester through local events, public art, and design projects.

Facebook Ovaicon-instagram

Events

Events

Events Search and Views Navigation

Event Views Navigation

Today

  • Find Waldo Local Begins!

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

    It's time for another round of Find Waldo Local! All month long, he'll be sneaking around Old Town businesses. Find him for a chance to win big!

  • Monty Python Pub Crawl

    Loudoun Street Pedestrian Mall

    🏰 HEAR YE, HEAR YE, brave souls of the Shenandoah Valley! ⚔️ The Holy Grail has been hidden somewhere in Old Town Winchester… and we need a fellowship worthy of the quest. 🗓️ Friday, July 17, 2026 📍 Old Town Winchester, VA 🍺 A Monty Python Pub Crawl: A Quest for the Holy Grail Follow […]

    Free

  • The All-American Pig & Pour

    Youth Development Center 302 S Loudoun Street, Winchester, V, United States

    Presented by Heaven Hill Distillery and Partlow Insurance, the All-American Pig & Pour returns to the YDC on Saturday, July 18 for one of Winchester’s favorite summer traditions. Blending upscale Americana charm with the energy of a summer backyard gathering, the All-American Pig & Pour brings the community together for an evening filled with bourbon, […]

    $40

  • Summer Art Class

    Summer Art Class
    Youth Development Center 302 S Loudoun Street, Winchester, V, United States

    Our Summer Art Series at the YDC is a fun, creative opportunity for kids to explore, learn, and express themselves in a welcoming environment. Made possible by the generosity of our donors, this program is offered free of charge to families in our community. Each week features a new project designed to inspire creativity, build […]

    Free

  • Summer Art Class

    Summer Art Class
    Youth Development Center 302 S Loudoun Street, Winchester, V, United States

    Our Summer Art Series at the YDC is a fun, creative opportunity for kids to explore, learn, and express themselves in a welcoming environment. Made possible by the generosity of our donors, this program is offered free of charge to families in our community. Each week features a new project designed to inspire creativity, build […]

    Free

  • Author Event: Michael Amos Cody – Avalon Moon

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

    We're excited to welcome back author Michael Amos Cody. In Avalon Moon, a local man has gone missing and then is soon found dead in a highland meadow, side-by-side with an unknown woman. When another man and woman go missing and a female deputy is found murdered, Gabriel Tanner, editor of Runion’s weekly newspaper, and […]

  • Summer Art Class

    Summer Art Class
    Youth Development Center 302 S Loudoun Street, Winchester, V, United States

    Our Summer Art Series at the YDC is a fun, creative opportunity for kids to explore, learn, and express themselves in a welcoming environment. Made possible by the generosity of our donors, this program is offered free of charge to families in our community. Each week features a new project designed to inspire creativity, build […]

    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 ????? ????????? ????????? ????????? ??????????? ?????, a ???? ??????? ????? ???? ?? ??? ??????. This October, attendees will be able to receive Acudetox (ear acupuncture), a technique used in addiction recovery to help reduce cravings, […]

    Free

  • First Friday

    First Friday
    Winchester Downtown Walking Mall Winchester, V, United States

    Friday nights are back in Old Town Winchester. Join Friends of Old Town for First Fridays, a monthly community celebration bringing live music, local artists, vendors, pop-ups, food, shopping, and extended downtown energy to the Walking Mall throughout the summer and fall. Each First Friday features: Live music at Taylor Pavilion Local artists and makers […]

    Free

  • Shift Happens: Driver Safety & Preparedness Day

    Cody's Auto LLC 32 w cecil st, Winchester, VA, United States

    Hands-on vehicle safety tips, emergency preparedness, giveaways, and confidence-building skills for every driver. Hands-On Tips. Real Confidence. Zero Judgment. Because “I have no idea what that light means” isn’t a roadside assistance plan. Join us for a fun, hands-on community event focused on helping drivers feel more confident, prepared, and safer on the road. Whether […]

    Free

  • Dawg Days of Summer: Old Town Hot Dog Crawl

    Loudoun Street Pedestrian Mall

    Get ready for a fun, self-guided crawl through Old Town where participating businesses serve up their own creative takes on the classic hot dog. Check in, grab your map, and make your way from stop to stop tasting, exploring, and discovering new spots along the way. Along the crawl, you’ll vote for your favorites, compete […]

    $30

  • You Should Be Dancing – Free Community Dance Night

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

    Dance Night is like a pop-up dance party. For two hours, we'll trade stress for smiles, screens for real people, and worries for rhythm. We'll spin a fresh mix of funky favorites, grooves through the decades, and some of your song requests -- all designed to bring the fun and keep the dance floor moving. […]