Explore Old Town
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 Art Walk, 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.