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; 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. (Closed for the 2020 season)
• The public restroom’s hours are 8am to 8pm, 7 days a week. (Updated 9/5/2020)
• 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.