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  Our son is playing baseball at Shenandoah University so we will be frequenting the area for the next 4 years 🤞🏼. As small business owners we love to support other small business owners and this tour was PERFECT for showing us hidden gems that even several locals said they had never tried. We appreciated the owners meeting us and telling us all about their wonderful offerings. The food was great, the tour guides were fun & knowledgeable & the owners were gracious. We loved this tour & even made new friends we hope to see on our many trips back to Winchester. Highly recommended!

    Paula Faivre Avatar Paula Faivre
    February 16, 2020

    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 had a great History and Hops tour! It was nice to get a tour of downtown Winchester from a local and learn history along the way! The beer was delicious. I highly recommend booking a tour!

    Genna D'Antonio Avatar Genna D'Antonio
    November 11, 2019