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  • Author Event: Bryan Lienesch – Happyland

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

    Stop by the Book Gallery to meet thriller author B. C. Lienesch and celebrate his latest publication! Dive back into the world of Jackson Clay with brand new mysteries and […]

  • Celebrating the Seasons: Holiday Events in Old Town

    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 […]

  • British Bingo

    British Bingo
    The Cider House 30 E Piccadilly St, Winchester, V, United States

    British Bingo is going monthly! 🎉 Join us for British Bingo every third Thursday of the month at The Cider House! Hosted by our very own cidermaster, it’s totally free […]

    Free

  • Trivia at 50/50 Taphouse

    Trivia at 50/50 Taphouse
    50/50 Taphouse 29 West Cork Street, Winchester, Virginia

    Come out to 50/50 Taphouse in Winchester, Virginia every Thursday (except holidays) to play general trivia with all of your friends. Get your team together or challenge yourself. Trivia is […]

  • Karaoke with DJ Blue Nova

    Karaoke with DJ Blue Nova
    The Cider House 30 E Piccadilly St, Winchester, V, United States

    🎤 Karaoke Nights are coming to The Cider House! 🎵 Starting Wednesday, August 13, we’re teaming up with DJ Blue Nova for karaoke every other Wednesday night! Bring your best […]

    Free

  • Open Mic Talent Showcase

    The Cider House 30 E Piccadilly St, Winchester, V, United States

    Have you got talent? Want to try your hand in front of a live crowd? The Cider House is having an Open Mic Showcase August 28! Unlike most open mics, […]

    Free

  • 15th Annual Patsy Cline Block Party

    Patsy Cline Historic House 608 South Kent Street, Winchester, V, United States

    Join us in celebrating Patsy Cline's Birthday and contribution to American Culture at our 15th Annual Patsy Cline Block Party on August 30th, 2025, between 10 am and 4 pm. […]

    Free

  • Anniversary Weekend British Bingo!

    The Cider House 30 E Piccadilly St, Winchester, V, United States

    It's The Cider House's one year anniversary on Labor Day Weekend! We're celebrating with British Bingo!

    Free

  • First Fridays

    First Fridays

    Discover the heartbeat of Old Town Winchester with Friends of Old Town’s First Fridays! From June through October, kick off your weekend each month with live music, local art, and […]

  • ShenArtsFest

    Old Town Winchester, VA is a beautiful venue for a festival with dedicated crowds and wonderful staff and volunteers. We hope you will apply!​ The Shenandoah Arts Council (ShenArts) is […]

    Free

  • Author Event: Leah Rampy – Earth & Soul

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

    Amidst accelerating climate devastation and an uncertain future comes a clarion call to renew a deep and personal relationship with Earth. Facing directly into the devastation of climate chaos and […]

  • Fiddles & Fifths – Bluegrass & Bourbon Festival’s

    Join us at the Old Civil War Museum in downtown Winchester for a free day of live music, local flavor, and bourbon tastings. 🎶 Featuring performances by: 🔥 The Bridge City Sinners 🎸 Brennan Edwards & The Monday Blues 🎻 Reno & Dunlap Music kicks off at 2 PM, and bourbon tasting tickets will be […]

    Free