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  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  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.

    Christie Brown Arnold Avatar Christie Brown Arnold
    September 11, 2018

    positive review  We did the Taste of Winchester food and history tour today for my husband, Mike Gooden's birthday. It was very informative and enjoyable! Our hosts, Misty and Anthony, knew all of the restaurant owners and provided a wonderful way for us to try the different ethnic and American options right there on the pedestrian walkway...places we wouldn't have really noticed otherwise. We highly recommend the tour, especially if you are looking to expand the list of restaurants you frequent!

    Margy Weidenbruch Nolan Avatar Margy Weidenbruch Nolan
    January 12, 2020