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  • HalloWinchester Pub Crawl

    Loudoun Street Pedestrian Mall

    Winchester’s biggest Halloween street party is back! Live music, alien vibes, $500 in costume prizes + raffle gift basket — all benefiting Katie’s Comfort House.

    $10

  • Halloween Costume Dance Party

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

    Join us Friday October 31st from 8pm until close for a night of thrilling dance moves & spooky Halloween costumes! DJ Chris Jarrell, photobooth, costume contest, drink & food Specials, […]

    free

  • Author Event: Dale Watten – Dream Valley Shenandoah

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

    Local author Dale Watten has a new book that showcases the native and naturalized flowers of the Shenandoah Valley in Western Virginia. Written in verse, it is accompanied by beautiful […]

  • Author Event: Jimmy Proffitt – Seasoned in Appalachia

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

    Inspired by home-cooked family meals, Seasoned in Appalachia delivers authentic, flavorful dishes paired with charming anecdotes about family traditions and the magic of the Appalachian region. Author and IACP member […]

  • Community Connections: Strengthening Old Town Together

    Winchester Brew Works

    We love hearing from our amazing Old Town community! That's why Friends of Old Town is hosting monthly outreach and input sessions all year long. These laid-back, open-forum meetups are […]

  • Wine tasting at Murphy Beverage Company

    Murphy Beverage Company 167 N Loudoun Street, Winchester, V, United States

    Come join us for a free wine tasting where Lisa of LK Wines will pour four wines that would be perfect for your Thanksgiving table - and beyond.

    Free

  • Author Event: Erika Santiago – You Are Not Alone

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

    Life has a way of breaking us open. For many women, motherhood, loss, and heavy seasons of survival can leave us feeling unseen, unheard, and disconnected from who we once […]

  • Plaid Friday 2025

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

    “Plaid Friday” is the idea of weaving individual threads of small businesses together to create a strong fabric! Today, we celebrate independent businesses while wearing our favorite leisure wear: plaid! […]