Dine, Shop & Explore

Dine, Shop, Explore

If you’re tired of traffic and the suburbs, you will love your visit to Old Town. Come enjoy a wonderful meal on the Walking Mall; eat at an outdoor cafe and watch people stroll by or dine in a sumptuous dining room with a crackling fire. No matter the season or your dining preference, Old Town Winchester has something for you. And after your meal, visit our unique shops, enjoy a drink or an ice cream cone, stroll down shady streets, and enjoy the feeling of nostalgia here. It’s like coming home.

Tips for Visiting Downtown:

  • Park in one of the four convenient Autoparks and spend a few hours exploring on foot.  (Check out a map of Old Town Winchester and parking info here.)
  • Best day to shop: Friday or Saturday — Most Quiet Day — Sundays (a great day for a quiet stroll around the historic district)
  • Don’t miss: Handley Library, the George Washington Hotel, Mt. Hebron Cemetery.
  • Come for a Special Event: First Fridays Celebration of the Arts, FIRST Friday of every month, except January and May; Bluemont Summer Concerts – 8 Saturdays during summer; First Night Winchester – New Years Eve annually; Shenandoah Apple Blossom Festival – annually each May; Wine & Fine Art Festival – annually each May.
  • Check out our Downtown Guide for a quick glance at shops, parking, and more.
  • Come cool off at our new Splash Pad located on the south end of the Pedestrian mall. The Splash Pad runs Sunday through Thursday from 10:30am to 10pm and Friday through Saturday from 10:30am to 12am.
  • The public restroom’s hours are Monday through Thursday from 8am to 9pm, Friday and Saturday from 8am to 11pm, and Sunday from 10am to 9pm.
  • Many businesses in Old Town Winchester offer discounts to students of Shenandoah University and Lord Fairfax Community College. Click here for a full list of participating businesses.
  • Get a quick overview of downtown’s layout with this  Old Town Winchester Map.


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