Loudoun Street Pedestrian Mall

Hark and gather, ye merry souls! On Saturday, March 14th, Old Town shall be awash in music, mirth, and Celtic cheer as we proclaim a grand celebration — Celtic Fest! […]

🍫 Chocolate Escape is coming to Old Town Winchester on Saturday, February 7th! Treat yourself (and your friends) to a sweet stroll through downtown with chocolates, treats, and fun surprises […]

Old Town on the Rocks January 16–18, 2026 | Old Town Winchester Old Town on the Rocks is a weekend-long bourbon and cocktail competition celebrating the creativity of Old Town […]

Join us in historic Old Town Winchester for a day of celebration culminating with a spectacular and FREE New Year’s Eve Neon Nights & Laser Light Show at the Old […]

Hop aboard the sweetest stroll in Old Town! On Saturday, December 13, our shops turn into cookie stations — each with a festive treat waiting just for you. Wander the […]

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.

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 […]