Historic Winchester Food Tour

What to Expect on the Tour

You’ll experience Old Town Winchester with a new eye on this tour. Explore the significance of buildings you’ve walked by before, hear about the men and women that made Winchester come to life, and sample food from Old Town’s unique restaurants along the way.

We’ll make sure you have fun with interesting historical facts, pointing out the best architecture, and telling you the stories behind the chefs. All of the food is included in the tour price, and we throw in the laughs for free!

Explore 5-6 Unique Stops

Winchester’s eclectic collection of restaurants continues to grow. This tour will take you on a taste sensation through samples and stories about how they got started and why you should come back again and again. Here are a few we might pop into on your tour:

The Hideaway Cafe

Fresco Kitchen

Benny Meleto’s

Espresso Bar and Cafe

Moe’s Donuts

Fellowship of the Sip, Organic Tea House

Sexi Mexi Burrito Bar

The German Table

Tropical Island Coffee & Cafe

Java Kava


    positive review  We had such a good time touring with Anthony and Misty on a rainy Sunday afternoon doing the History & Hops tour! We stopped at four places, and learned about the breweries, the beer, and a bit of Winchester history as well. They had a good relationship with each of the establishments and really catered to us in every way - from recommending beers to our palettes, taking our orders, and cleaning up afterwards, it was really above and beyond what you would expect from your tour guides. They are great conversationalists who will feel more like fast friends by the time your tour has ended. We will definitely try the Food tour that they offer the next time we are in Winchester for the holidays!

    Emmy Gottschalk Avatar Emmy Gottschalk
    December 30, 2019

    positive review  The tour was fun, delicious, and informative. We are our way through the walking mall and got to try new places and new dishes. We loved Misty and Anthony who were our guides. It was an awesome day date!

    Katie Landi Jordan Avatar Katie Landi Jordan
    April 7, 2019

Frequently Asked Questions

Where does the tour meet?
Exact location will be provided on your tickets.
Do tickets have to be purchased in advance?
Yes – we need to let our breweries and restaurants know how many tour guests to expect so tickets must be purchased at least 4 hours in advance.
Are children welcome on the food tour?
Absolutely! We suggest children be at least 10 years old, but parents are welcome to use their judgment for their own children and whether they can handle a three hour tour.
Tour Conduct
  • Participants may reschedule their tour for a new date with 7-days’ advanced notice. There are no refunds.
  • Participants are expected to behave respectfully to others including, but not limited to guides, other tour participants, members of the public, and towards the property of others, including but not limited to shared facilities and public environment.
  • Participants are expected to obey all local, federal, and Commonwealth of Virginia laws. Violations of any law is grounds for dismissal from the tour without a refund.
  • Drunk and/or Disorderly Conduct is grounds for dismissal from the tour without a refund.
  • Taste Winchester History reserves the right to stop a tour if participants violate the Code of Conduct. No refund will be given, and the participants must pay the full compensation for any damages that might have been caused.
  • This Code of Conduct is outlined as such and serves as a guideline for all Taste Winchester History participants to follow. We want all participants to have a fun and interesting time and enjoy what Winchester, Virginia has to offer. Your cooperation and patronage are appreciated.
How much walking is involved?
We stay within two blocks of the Old Town Walking Mall. Total walking is about a mile as we traverse the mall.
What should I wear?
We will be indoors for most of the tour but will be walking outside to get to the next destination and for quick historical and architectural stops, so please wear clothes appropriate for the weather, and bring an umbrella if rain is in the forecast.
Is this tour good for local Winchester residents?
Absolutely! We tend to find that the closer we live to something the less we explore! Locals will learn new things, and our restaurants often offer new menu items to our guests.
Can I schedule a private tour?
Absolutely! Reach out to us at info@tastewinchesterhistory.com