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.

Secret Chef Dinner

Make sure you are on the list for what will be the best dinners of the year! Our Secret Chef Dinner series are private, intimate, unique themed dinners in unexpected places around Winchester. We’ll be taking you to some of the most historic homes and unique buildings, while eating creative menus! By invite only, so get on the list now!

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 sample 5-6 unique dishes.

Sat, 2PM
2.5-3 Hour Tour
$55

History and Hops Beer & Cider Tour

Ready to see the other side of Winchester? Learn about the strong women and how architecture has changed Winchester’s historic landscape while you sample beer and cider from our downtown breweries.

Sun, 2PM
2.5-3 Hour Tour
$65

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

    Eileen Curtis Avatar Eileen Curtis
    August 25, 2019