History • Architecture • Food • Beer

Experience Winchester VA Like Never Before

Discover Winchester one step, sip, bite at a time!

Explore the city’s unique and thriving food scene on our downtown Winchester walking mall food tours. Your experienced guide will introduce you to great local dishes and drinks while sharing stories about Winchester’s rich history and architecture.

Self Guided Historic Food Tour

Explore Winchester in this one of a kind historic food tour where you’ll learn about the founding events of Winchester, local architecture, and visit 5-6 restaurants. 

Fri, Sat, Sun
$25 per group

    positive review  We had a great time on this food/history tour! Misty and Tony make a great team together. As I have not grown up in America the history information was so interesting for me to learn. Starting the tour at the Hideaway Cafe was great . Excellent sandwiches and good coffee to start . The different restaurants were amazing. I recommend this tour so much .

    Torsten Kiesewalter Avatar Torsten Kiesewalter
    September 15, 2018

    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

    positive review  Great way to spend an afternoon: learning about the Winchester Historic District and enjoying samplings from the diverse collection of restaurants in the area. Our Guide, Anthony, was spectacular! Try the meatballs and mashed potatoes at the Fellowship of the Sip. Absolutely delightful!

    Jani Wright Avatar Jani Wright
    August 13, 2019