Shopping & Dining

Old Town mall, 2
Old Town water feature

Shopping in Old Town Winchester is an experience to be savored. Old Town is sure to have just what you’re looking for – an eclectic mix of antiques, fine furnishings, gift items, local and regional works of art, and fine clothing.

Old Town Winchester is located within the heart of a 45-block National Register Historic District and features a quaint pedestrian walking mall bursting with outdoor cafes, fun shops, specialty retail boutiques, and family-oriented activities throughout the year.

Enjoy a variety of restaurants featuring outdoor cafe dining, or dine in and enjoy the ambiance of our many historic settings.