Cheesin' for a Reason 2025

📅 Saturday, November 8, 2025

📍 Old Town Winchester - enter the downtown walking mall at Rouss Avenue off of N. Cameron Street to check-in and get your wristband

⏰ 11:00 AM - 5:00 PM (you will only be permitted to enter at your ticket time, not before)

💵 Tickets: $20.00 for adults, $10.00 for children 12 & under
(includes tastings at 15+ restaurants, voting for your favorites, live music, kids activities, shopping & vendors, and more!)

Anticipated to be the next biggest and beloved event in downtown Winchester, enjoy taking in the entire length of the walking mall on a crisp, fall day to visit the participating restaurants and food trucks for your samples of the comfort food: grilled cheese and tomato soup! There will be a kids zone with a variety of free activities (included with your ticket purchase) as well as vendors at which to shop and live music throughout the day, centrally located near the Civil War Museum. We'll also be doing a scavenger hunt — similar to the "Where's Waldo" challenge, pop into participating shops and look around for the item. Spot them all for a chance to win a prize! Commemorative event t-shirts and merch will be for sale, and don't miss the 50/50 raffle, and more. A memorable and mouth-watering event that promises to be a lively, fun community day for all, we hope you'll join us and come together to make an incredible impact for adults experiencing homelessness in our community. Together, we're breaking the cycle of homelessness one life at a time through our shelter program and vital support services for our guests - THANK YOU for helping make a difference in the lives of those who need it the most!

NOTE: No tickets will be sold on the day of the event - must be purchased in advance.

*BEWARE OF SCAMMERS - Always be wary of anyone on social media offering to "sell" their tickets for one reason or another. Only purchase from WATTS directly through this our event site. If you need to transfer your tickets to another name, please contact us prior to the event - no one other than the names listed at purchase will be admitted to the event.

SPONSORSHIPS AVAILABLE!
Advertise your business or organization at this event! Click the sponsor button to learn more or reach out to us today.

VENDOR SPOTS AVAILABLE!
(Crafts, trinkets, gifts, hand-made items, product sales, etc. - Not for food vendors/trucks.) Location will be central on the walking mall, near the Civil War Museum - great exposure, just 6 weeks prior to Christmas. 10 x 10 spots; no electric, bring your own table, chairs, tent, etc. Limited to 20 spots, so pay the vendor fee under 'Ticket Details' to reserve your spot today!