Cheesin' for a Reason 2025

November 8, 2025 @ 11:00AM — 5:00PM Eastern Time (US & Canada) Add to Calendar

Old Town Winchester - downtown walking mall: Rouss Ave Winchester, VA 22601 Get Directions

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WATTS' 1st Annual Grilled Cheese and Tomato Soup Extravaganza for Winchester!

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 this classic, comfort food combo, voting for your favorites, and helping raise funds for a great cause ♥

📅 Saturday, November 8, 2025

⏰ 11:00 AM - 5:00 PM
(Ticketed entry times at 11AM, 1PM, and 3PM; you will only be permitted to enter at your ticket time, not before)

📍 Old Town Winchester - enter the downtown walking mall at Rouss Avenue (off of N. Cameron Street, between Truist Bank and Rouss City Hall) to check-in and get your wristband

💵 Tickets: $20.00 for adults | $10.00 for children 12 & under
**Tickets will NOT be sold at the gate - MUST be purchased in advance on this our event site**

*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 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 given a wristband. If you purchase a group of tickets, please come all together at your check-in time.

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 classic, comfort food: grilled cheese and tomato soup! Your ticket includes tastings at our 10+ participating downtown restaurants & food trucks. Our restaurants have been working hard on some neat twists and flair, crafting and combining the perfect flavors that are sure to wow your tastebuds - AND you'll get to vote on your favorites for the coveted titles of Best Sandwich, Best Soup, and Best Combo. There will be a kids zone with a variety of free activities included with your child's ticket purchase (magician Kevin Owens, face & hand painting by Michelle, balloon art, and a scavenger hunt at participating downtown shops!) as well as craft vendors at which to shop (start your Christmas shopping early!) and live music throughout the day with Ryan Jewel Band from 11:30-1:45 and Raised on Analog from 2:15-5:00. Commemorative event t-shirts will be for sale, and don't miss the 50/50 raffle, meet and take pics with the King & Queen of the Cheese Fest, and more!

A fun, community event to make an incredible impact - "Cheesin' for a Reason" has all the fixin's to make for a memorable and mouth-watering, ooey-gooey goodness kind of day for all that you WON'T want to miss! We hope you'll join us and invite a few friends, family, co-workers, neighbors, acquaintances, etc. Get your tickets TODAY and help us raise funds for a great cause to make a huge impact for our friends and neighbors who are experiencing homelessness in our community. THANK YOU for making a difference in the lives of those who need it the most!

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VOLUNTEER AT CHEESIN' - Click here to sign-up today!
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VENDOR SPOTS - SOLD OUT!
(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' spots; no electric, bring your own table, chairs, tent, etc.

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Participating Restaurants/Food Trucks:

Fleur de Lis Cheese Shop
Billy Sous
Water Street Kitchen
Sexi-Mexi
Red Fox Creamery
T. T. Wall's
Espresso Bar & Cafe
Manolete's
Knead Bread
Potato Sensations Food Truck

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Live Music Schedule:

-Ryan Jewel Band from 11:30-1:45
-Raised on Analog from 2:15-5:00
-DJ Tony Knave filling the in-betweens!

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Kids Activities:
(Included with your child's ticket purchase)

-Magician Kevin Owens
-Face & Hand painting by Michelle
-Balloon Art too!
-Scavenger hunt (for a small prize) at participating downtown shops:

Thinker Toys
Abija Blue
Faire Isles Trading Co.
Winchester Book Gallery
Exotic Himalayan Handicrafts
Handworks Gallery

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Vendors:

ShawnaRene's Creations
Stuff & More Stuff - Carolyn Dachenbach
The Overflow Soda Co.
EstRaeya Designs
Jacquetta Owen Creations
Sym Soaps
Lunar Garden Crystals
Omni Creations
Four R Farms LLC
Drunken Wicks Candles
Stephens City Lions Club apple butter & brooms
Apple Federal Credit Union
Blue Ridge Agents Insurance
Kiwanis of Old Town
Integrity Home Mortgage

A big thank you to our sponsors!

Title Sponsor
Johnny Blue Inc.
T-shirt Sponsor
Berry Hill Logistics LLC
Welcome Sponsors
Navy Federal Credit Union
Kids Zone
Ken & Nancy McKee Foundation, Inc.
Kiwanis Club of Winchester
Vendor Zone Sponsors
Apple Federal Credit Union
Bank of Clarke 2025
Blue Ridge Agents Insurance
TWG Insurance
Passport Sponsors
Kee Construction Services, Inc.
Ken & Nancy McKee Foundation, Inc.
Realty ONE Group Old Towne
Angela Brewer
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