Self Guided 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 owners.

Our self guided tour is perfect for any group that wants to explore even during our active pandemic. You will have complete control over your timeline and group as you meander through town with our guided videos and stops directly with your cell phone! You choose your day and starting time and just follow our advice.

The self guided tour includes tour access on one device, for one low cost for your entire group. Your food purchases are up to you so you can better control your budget and choose food items that fit you with recommendations from us so you can try something new or experiment and go outside your comfort zone a bit!

– Our self guided tours are $25 per group.
– Tour days and times are chosen by you, best on Fri, Sat, Sun
Cell phone is needed to follow the guide
– You have 15 days to complete the tour from time of purchase

NOT BOOKING CURRENTLY – Please check back as we rework our tours with restaurants after the pandemic.

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 you might pop into on your tour:

The Hideaway Cafe

Gringo Gordo

Benny Meleto’s

Espresso Bar and Cafe

Fellowship of the Sip, Organic Tea House

Sexi Mexi Burrito Bar

Snow White Grill

Tropical Island Coffee & Cafe

Java Kava

Frequently Asked Questions

How many people can be included in the self-guided tour?

We have not put a limit in place but request guests keep their groups lower than the current suggested group gatherings suggested by the CDC. Groups lower then 10 people are best for our restaurants in any case as many are smaller in size.

Is food included on the tour?

On our self guided tours the food is NOT included. This gives you more flexibility for taking the tour on your own time, and choosing what fits your personal budget. 

Is the price per person or group?

Our self guided tours are priced per GROUP! This is a great discount so you can enjoy our tours on your own as a group. Food is NOT included in our self guided tours, you will need to purchase your own food at each restaurant. We include suggestions and some restaurants have specials for our tour guests.

Where does the tour meet?

Exact suggested starting location will be provided in your tour account.

Do tickets have to be purchased in advance?

Yes – our self guided tours need to be purchased before starting the tour, but can be done so moments before, though we do suggest at least 24 hours in case you have problems logging into your account!

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 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. This includes all Covid guidelines.
  • 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 an in person guided tour?

We hope to be back to in person tours as soon as things return to normal.

Recent Reviews

    positive review  I have loved living in Winchester for the past fifteen years, but today, I fell in love with it all over again! We did the food and history tour given by Misty and Anthony, a dynamic duo! We immensely enjoyed being in their company and all the amazing food and history that they presented to us. They have wonderful relationships with the owners of the restaurants, who personally gave us beautiful presentations of their food and history of their restaurants. We felt so welcomed by everyone we met and made to feel like part for he community. We are looking forward to taking other tours that you are working on. Thank you so much for all the time and love you have invested in this little town we call home;)

    Cari A. Brown Avatar Cari A. Brown
    January 26, 2020

    positive review  As others have said, Misty and Anthony are the engaging hosts who toured us through downtown Winchester. Although I live in the area, I was pleasantly surprised by the delicious restaurants we sampled. We got to meet the restaurant owners who were so excited to have our tour visit them. The historical tidbits have me seeing Winchester in a whole new perspective. This is a great activity for locals and tourists alike!

    Linda Bogart Avatar Linda Bogart
    October 31, 2018