🎃 Trunk or Treat on Loudoun Street 📅 Saturday, October 18, 2025 🕓 4:00 – 7:00 PM 📍 302 S. Loudoun Street, Winchester, VA (YDC Parking Lot) FREE & open to all - thanks to our generous YDC donors! 👻 Join us for a spook-tacular evening of safe, family-friendly Halloween fun right in the heart of […]

Bring the family to Old Town Winchester for a safe and festive afternoon of trick-or-treating! Local merchants along the Loudoun Street Pedestrian Mall will be handing out candy and goodies to children in costume. Stroll through downtown, show off your Halloween spirit, and enjoy the seasonal decorations, shops, and restaurants that make Old Town such […]

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.

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, and candy for the kids (or adults too)!

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 watercolor illustrations, depicting twenty four common wildflowers and their habitats. Come say hi and get your signed copy.⁠

Our 1st Annual Grilled Cheese and Tomato Soup Extravaganza for Winchester! 🧀🍅 WATTS will be "Cheesin' for a Reason" this fall and we hope you'll come out and join us in honor of one of our guests' favorite meals. Your ticket includes tastings/samplings of this classic, comfort food combo (with some flair!) from 15+ restaurants […]