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

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    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  Our hosts were great and knowledgeable about Winchester's history and the types of beers we were drinking. The beer was plentiful! It was great to have places to eat in between even thought I couldn't eat another bite, I could've gone for another plum tart beer. Thank you for an enjoyable afternoon. -Cathy

    Kitkatja Astrid Brahms Avatar Kitkatja Astrid Brahms
    July 16, 2019

    positive review  Wonderful hosts, fascinating history, delicious foods. We thoroughly enjoyed our time and highly recommend.

    Eileen Curtis Avatar Eileen Curtis
    August 25, 2019