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.

Valentine’s Dessert Tour

The perfect date for your special someone! We’ll be sampling desserts at five restaurants and finishing off with a champagne toast and rose for the ladies! Space is VERY limited!

Sat Feb 16, 2PM
Sun Feb 17, 2PM
2 Hour Tour
$50

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

    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 .

    thumb Torsten Kiesewalter
    9/15/2018

    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.

    thumb Christie Brown Arnold
    9/11/2018

    The food/history tour of Winchester was great. So much delicious food/beverages and little bits of local history. Really recommed this!

    thumb Hollynn Kidwell
    10/10/2018