Loudoun Street Pedestrian Mall

Events at this venue

Today

  • 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

  • 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