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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 […]

    $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 […]

  • 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 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 […]

    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 […]

  • 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 […]

  • 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 […]