Cheesin' for a Reason - a grilled cheese & tomato soup extravaganza

Join WATTS in Cheesin' for a Reason! Named in honor of one of our guests' favorite meals you'll enjoy a fun day for the whole family tasting/sampling a variety of twists on the classic comfort food combo of grilled cheese & tomato soup voting for your favorites and helping raise funds for a great cause ♥

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. 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 challenge - pop into the participating shops downtown 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.

📅 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 (entry times at 11AM 1PM and 3PM; 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 10+ restaurants voting for your favorites live music kids activities shopping & vendors and more!)

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*BEWARE OF SCAMMERS - Always be wary of anyone on social media offering to "sell" their tickets; there are no physical tickets for this event. Only purchase from WATTS directly through 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. If you purchase a group of tickets please come all together at your check-in time.

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SPONSORSHIPS AVAILABLE!

Advertise your business or organization at our event! Click the ticket link and hit the button for 'sponsor our event' to learn more or reach out to us today.