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

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

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

    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

    Absolutely wonderful way to spend an afternoon! We experienced a wide variety of amazing food, coffee, and tea. Definitely come hungry, you will not be disappointed! I also learned a lot about Winchester’s history that I never knew before! Anthony and Misty are fun and knowledgeable! What a fabulous, memorable experience!

    thumb Kris Reichert

    I'm a little biased because I am one of the guides, but I am giving this rating just to let everybody know how wonderful our tour stop hosts are. The owners, the chefs, the cooks, the staff are all very knowledgeable and engaging, the food is wonderful, and we have as enjoyable a time as our guests. So please do feel free to join us and experience what our business owners have to offer both locals and visitors. And as always we thank you all for your patronage.

    thumb Anthony Morelli