Business Directory

Lodging & Transportation

Winchester is the perfect place to stay as you explore the Shenandoah Valley. Here you’re close to vineyards, historical attractions, Virginia hunt co...

COVID-19 Directory

Many Old Town businesses are open and waiting to serve you with the same hospitality and superior service you’ve come to expect. Please know that the ...

Old Town Winchester is a true Main Street Community. We have a charming, eclectic mix of businesses all within easy walking distance: from museums and fine dining, to unique shops and historical B&Bs. Come visit, shop, live or work in Old Town.

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Dining & Libations Alphabetical list:

50/50 Taphouse 29 W. Cork St. 540-773-4986

147 North 147 N. Loudoun St. (540)-313-4084

Alesation Brewing Co. 23 N. Loudoun St.(540)667-2743

Aroma Deli and Coffee Bar 201 East Boscawen St. (540)545-4627

Awabi Sushi Bar 111 S. Loudoun St. (540) 686-7432

Benny Meleto's 19 E. Boscawen St. (540)323-7036

The Black Rose Coffee & Tea Lounge 11 South Loudoun St. (540)542-6160

Brewbaker's Restaurant 168 N. Loudoun St. (540) 535-0111

Broken Window 14 W. Boscawen St. (540)860-0849

Chopstick Café 207 N. Kent St. (540)450-8691

Cork Street Tavern 8 W. Cork St. (540) 667-3777

El Centro 1 N. Loudoun St. (540) 313-4583

Espresso Bar and Café 165 N. Loudoun St. (540) 686-7209

'Fellowship of the Sip’ Restaurant & Tea House 33 S. Loudoun St. (540) 699-0777

Fresco Kitchen 6 S. Loudoun St. (540)664-5541

George's Food and Spirits 103 E. Piccadilly St. 540-678-4700

The German Table 158 N. Loudoun St. (540)431-5861

The Half Note Lounge 103 E. Piccadilly St. 540-678-4700

The Hideaway Café 141 S. Loudoun Street (540)450-0799

Italian Touch Pizza 229 S. Loudoun St. (540)667-0008

Java Kava 16 S. Loudoun St. (540) 313-7199

La Nicoise Café 12 S. Braddock St. (540) 722-4557

Lloyd’s Tropical Island Coffee and Café 39 W. Piccadilly St. (540) 905-8022

Macado’s 121 N. Loudoun Street (540) 323-7162

Milano's Ristorante & Bar 107 w. Boscawen St. (540)665-9437

Moe's Donut Shop 28 E. Piccadilly St.(540)300-8655

Old Town Snow White Grill 159 N. Loudoun St. (540) 722-7141

Piccadilly Grill Diner 46 E. Piccadilly St. (540) 667-4021

Piccadilly's Public House and Restaurant 125 E. Piccadilly St. (540) 535-1899

Red Fox Creamery 146 N. Loudoun St. (540) 545-8630

Roma's Old Town Wood-fired Pizza 21 N. Loudoun St. 540-667-2743

Sexi Mexi Burritos 21 E. Boscawen St. (540)773-8521

Steamy's Café 38 E. Piccadilly St. 540-664-9415

Thai Winchester 24 S. Loudoun St. (540) 678-0055

Union Jack Pub & Restaurant 101 N. Loudoun St. (540) 722-2055

V2 Raw Bar 103 N. Loudoun St. (540) 667-8961

Village Square Restaurant 103 N. Loudoun St. (540) 667-8961

Violino Ristorante Italiano 181 N. Loudoun St. (540) 667-8006

Water Street Kitchen 2 S. Loudoun St. (540) 313-4680

Winchester Brew Works 320 N. Cameron St. (540)692-9242