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Old Town Winchester, VA

Purple Star emoji 13 items
Downtown walking mall + more
Map
Sections
5
 
 
 
 
 

Breweries + Beer 🍻

 
Jennifer Aufdenberg profile picture
Dog friendly + gluten removed beer (using enzyme process). No food onsite, but can order food for delivery.
Broken Window Brewing Company
 
Jennifer Aufdenberg profile picture
Off the walking mall, but same owners as Dividing Creek
Escutcheon Brewing
 
Jennifer Aufdenberg profile picture
On the walking mall. Dog friendly, indoor/outdoor seating. No food, but may bring your own.
Dividing Creek Beer Co.
 
Jennifer Aufdenberg profile picture
Small brewery on the walking mall next to bright box. Good food (gluten free options). Brewery is upstairs, but you can order from Roma’s below. Seltzer option for gluten free, and wine I believe.
Alesatian Brewing Company
 
Jennifer Aufdenberg profile picture
Gluten free options available. Brewery and full restaurant. Cocktails + Coffee ☕️🍹
Vibrissa Beer

Adult Things + Cocktails 🍸

 
Jennifer Aufdenberg profile picture
You just need to go
Home | The Wine Room at Taylor Pavillion

Food + Drinks 🍻🍔

 
Jennifer Aufdenberg profile picture
Mexican restaurant at the intersection of the walking mall. Bonus: They will walk over food to Broken Window.
El Centro
 
Jennifer Aufdenberg profile picture
Delicious. Can make almost anything gluten free! They’ll also walk food down to broken window brewing company. Very good, I worded here far too often. Great customer service and food.
Sabai Thai Winchester

Cool Finds 😎

 
Jennifer Aufdenberg profile picture
Cool gluten friendly cafe at the end of the walking mall 🐈 Coffee + Cats. **Reservations needed for interaction with the cats.
Biscuits & Beans Cat Café | Winchester, VA
 
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Live music and events
Bright Box Theater
 
Jennifer Aufdenberg profile picture
I wouldn’t know how good this place is, but it smells freaking amazing. People brought it into the brewery (broken window) often and it smells incredible. People seem to love them.
Benny Meleto's
 
Jennifer Aufdenberg profile picture
Haven’t tried it, but my son liked it!
Worlds Away Escape

For Kids

 
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**TEMPORARILY CLOSED** Under repair, may be closed for the entirety of summer 2026
Old Town Splash Pad