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  • 90’s-00’s Music Trivia @ Dividing Creek

    Dividing Creek Beer Co 160 N Loudoun St, Winchester, VA, United States

    Break out the butterfly clips, cargo shorts, and burned CDs—it’s time for a night of 90s & 2000s Music Trivia! From boy bands and pop princesses to grunge, hip-hop, emo, […]

  • 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. […]

  • YDC Community Flow

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

    YDC Community Flow is a weekly adult vinyasa yoga class designed to support physical wellness, mental clarity, and meaningful connection. Beginning September 1, this ongoing Tuesday evening class invites adults […]

  • 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

  • Author Event: David Randal – Kelsey’s Crossing

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

    In his quest for redemption from past sins, disgraced political consultant and ex-convict Greg Smith agrees to assist the men at the Kelsey Rescue Mission in saving their homeless shelter from corrupt city officials determined to shut it down. The resulting acts of revenge and violence, including murder and kidnapping, could not have been anticipated. […]

  • 16th Annual Patsy Cline Block Party

    Patsy Cline Memorial Park 220 E Pall Mall Street, Winchester, VA, United States

    Celebrating Patsy Cline, Inc. and the Patsy Cline Historic House invites you to the 16th Annual Patsy Cline Block Party, a free community event on Saturday, September 5, 2026, from 11 AM to 5 PM! Get ready to go “A-Walkin’ Out in the Patsy Cline Memorial Park” 11 AM to 5 PM on Saturday, September […]

  • YDC Community Flow

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

    YDC Community Flow is a weekly adult vinyasa yoga class designed to support physical wellness, mental clarity, and meaningful connection. Beginning September 1, this ongoing Tuesday evening class invites adults of all experience levels to explore movement, breath, and mindfulness in a welcoming and inclusive environment. Each 75-minute session is thoughtfully structured to guide participants […]