• Apple Blossom Mall

    Indoor shopping mall with over 90 stores, food court, children’s play area, and an AMC movie theater.

    Apple Blossom Mall
  • Blue Plate Books

    Blue Plate Books buys and sells gently used, out of print, and antiquarian books. Visit their collection of over 50,000 books every day from 11am-7pm.

    Blue Plate Books
  • Creekside Town Center

    Creekside offers a unique blend of outstanding national chain and independent retailers and dining venues. Shop, dine, or take a stroll along the brick sidewalks, and enjoy the best of both worlds: Main Street friendliness. City sophistication.

  • Eugene B. Smith Gallery

    Located in Old Town Winchester, the Eugene B. Smith Gallery showcases the watercolor work of Eugene B. Smith.

    Eugene B. Smith Gallery
  • Kimberly’s

    Since 1989, this boutique has been a staple of Old Town Winchester. The shop features men’s, women’s, and children’s clothing, personalized gifts, and items for the home.

  • Mountain Trails

    Mountain Trails is the premier outfitter for all your adventures. Quality apparel and equipment from brands like Patagonia, Chaco, Salomon, Mountain Hardwear, and more. Mountain Trails. Find Your Trail!

    Mountain Trails
  • Old Town Winchester

    Historic district with two-block pedestrian mall features an eclectic blend of boutiques, antiques, fine furnishings, art, and clothing. Loudoun Street between Cork and Piccadilly Streets.

    Old Town Winchester
  • The Homestead Farm at Fruit Hill Orchard

    Fifth generation family-owned market with handmade local gifts including candles, soaps, jewelry, wreaths, and primitive style home decorations.

  • Winchester Book Gallery

    This independent, locally owned bookstore has served the literary and intellectual interests of the community for more than 40 years.

    Winchester Book Gallery