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    Pretty mural

    I was hopeful based on online research. The shops seemed geared towards a hippie vibe. Rock shops, vape, vintage, and lots of bars. A lot of homeless, panhandlers, the aroma of pot, and not much to see or do. As someone else mentioned, the little water area is closed for the season. There was a nice small books store and outdoor supplies store. We ate at 2 restaurants that were not impressive. If you have nothing to do and want to kill an hour or two, it's a quaint place. There was a "Where is Waldo" scavenger hunt to entertain kids. Overall, one and done for us.

    Kathleen D.

    Winchester may just be one of my favorite towns in Virginia. I was first introduced to it back in high school when I visited Shenandoah University on a whim. It ended up being my second-choice school, so I didn't land there, but the town etched itself into my memory pretty strongly. I've been back a few times since, most recently this summer, and it always feels like such a calming experience to pull into the downtown area. The pedestrian mall is well kept with lots of cute shops and restaurants. I look forward to future visits in the future.

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    5 years ago

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    5 days ago

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    7 days ago

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    4 days ago

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    2 years ago

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    3 years ago

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    Old Town Winchester - landmarks - Updated July 2026

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