Winchester Specialty Food Tours

Valentine’s Dessert Tour

Enjoy a fantastic tour with your significant other this Valentine’s weekend! We’ll be stopping at 5 top secret locations to sample decadent desserts and ending with a champagne toast and roses for the ladies! Only two tours so space is very limited, book early!

Saturday February 16, 2-4pm
Sunday February 17, 2-4pm

Private Tours

Did you know we offer private tours? We can plan a tour for your large group whether you have vendors coming into town and need to entertain, are planning a girls weekend or bridal shower, or just need a place to hang with your family and friends we can put a private tour together for you that introduces you to Winchester and our fantastic restaurants and breweries. All on your schedule! Reach out to get more information!

Kids International Food Tour

Coming 2019! We are teaming up with the Discovery Museum to offer a kids food tour and play time! We’ll introduce you and your child to several international cuisines while we learn fun history facts about Winchester, and then you’ll be off to the museum to work off all your energy! Stay tuned! Reach out to get more information!

    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.

    thumb Christie Brown Arnold

    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!

    thumb Kris Reichert

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