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
Espresso Bar and Cafe
Fellowship of the Sip, Organic Tea House
Misty and Anthony were great hosts of this informative walking/eating tour of historic downtown Winchester. Hideaway Cafe amazing tea and coffee as well as tasty sandwiches. Delightful experience at Fellowship of the Sip to include chickpea scramble, spinach quiche. Off to Benny’s for delish pizza and socializing finishing the tour with some out of this world pumpkin spice latte and treats from Moe’s. Such a mouth watering taste bud adventure as well as some historical tie bits. Highly recommend this to anyone.
Absolutely wonderful way to spend an afternoon! We experienced a wide variety of amazing food, coffee, and tea. Definitely come hungry, you will not be disappointed! I also learned a lot about Winchester’s history that I never knew before! Anthony and Misty are fun and knowledgeable! What a fabulous, memorable experience!
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.
- 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 firstname.lastname@example.org