Guidebook for Winchester
Food Scene
Great food, nice outdoor seating area. Late night lounge-like setting next door at V2. That's "v-squared", get it?!
13 locals recommend
Village Square Restaurant
103 N Loudoun StGreat food, nice outdoor seating area. Late night lounge-like setting next door at V2. That's "v-squared", get it?!
Fish & chips! Among other authentic- English pub fare. Impressive beer selection. Has a "public hall" feel downstairs, cushy chairs on the landing upstairs.
20 locals recommend
Union Jack Pub & Restaurant
101 N Loudoun StFish & chips! Among other authentic- English pub fare. Impressive beer selection. Has a "public hall" feel downstairs, cushy chairs on the landing upstairs.
Local homemade icecream. Try the salted caramel. The main stores on the walking mall. But there's a Red Fox Creamery service window right on Cork Street, just yards from Levi Wickham House!
Red Fox Creamery
146 N Loudoun StLocal homemade icecream. Try the salted caramel. The main stores on the walking mall. But there's a Red Fox Creamery service window right on Cork Street, just yards from Levi Wickham House!
Recently celebrated in the Washington Post as not-to-be-missed in Winchester. You can smell the wood smokers for blocks. Generous portions of southern comfort food in a unique quirky setting.
28 locals recommend
Bonnie Blue Southern Market & Bakery
334 W Boscawen StRecently celebrated in the Washington Post as not-to-be-missed in Winchester. You can smell the wood smokers for blocks. Generous portions of southern comfort food in a unique quirky setting.
Delicious food, good service. They've recently moved into a beautiful new space along the railroad track on the northwest end of town, just off the walking mall. It's a 10 minute walk from the Wickham house but worth it.
13 locals recommend
Chop Stick Cafe
207 N Kent StDelicious food, good service. They've recently moved into a beautiful new space along the railroad track on the northwest end of town, just off the walking mall. It's a 10 minute walk from the Wickham house but worth it.
Shop for vinyl while you sip a latte. Nate roasts his own right in the building. Hint: You can get a Hop Scotch coffee at Bonnie Blue, too!
18 locals recommend
Hopscotch Coffee & Records
250 Millwood AveShop for vinyl while you sip a latte. Nate roasts his own right in the building. Hint: You can get a Hop Scotch coffee at Bonnie Blue, too!
Great coffee, good smoothies, and Lenny boils his own awesome bagels. The place has a "stick around and hang out" kind of feel, with quirky comfy furniture, much of it on consignment. Oh, and a chin-up bar...twenty chin-ups gets you a free cup of joe!
9 locals recommend
Steamy's Café
38 E Piccadilly StGreat coffee, good smoothies, and Lenny boils his own awesome bagels. The place has a "stick around and hang out" kind of feel, with quirky comfy furniture, much of it on consignment. Oh, and a chin-up bar...twenty chin-ups gets you a free cup of joe!
This is your classic neighborhood bar. Sadly, there was a fire recently, and the decor took a bit of a hit. They're coming back though. There's karaoke from time to time. Unless you're a smoker, be certain to choose the west (closer to the corner) dining room.
6 locals recommend
Cork Street Tavern
8 W Cork StThis is your classic neighborhood bar. Sadly, there was a fire recently, and the decor took a bit of a hit. They're coming back though. There's karaoke from time to time. Unless you're a smoker, be certain to choose the west (closer to the corner) dining room.
Popular destination for Thai food on the walking mall. There's sidewalk dining for those interested in eating al fresco, but watch out, the guy frequently busquing outside seems to have only one volume...LOUD! Regulars have watched the owner's baby daughter grow up in the booth by the kitchen.
21 locals recommend
Taste Winchester History
149 N Loudoun StPopular destination for Thai food on the walking mall. There's sidewalk dining for those interested in eating al fresco, but watch out, the guy frequently busquing outside seems to have only one volume...LOUD! Regulars have watched the owner's baby daughter grow up in the booth by the kitchen.
Stop judging, all you city slickers! There may be more canons than cucumber roles in Winchester, but Awabi is the real deal. Grab a Bento Box at lunchtime. Open wide for the Lollipop Roll.
8 locals recommend
Awabi Sushi Bar
111 S Loudoun StStop judging, all you city slickers! There may be more canons than cucumber roles in Winchester, but Awabi is the real deal. Grab a Bento Box at lunchtime. Open wide for the Lollipop Roll.
The coffee is pretty good, and the setting is pleasant. Don't miss the patio out back. For fans of repurposing, the Lovett Building is a great example, a little cavernous but beautifully renovated. Grab a latte and head over to the Book Gallery next door!
8 locals recommend
Espresso Bar & Cafe
165 N Loudoun StThe coffee is pretty good, and the setting is pleasant. Don't miss the patio out back. For fans of repurposing, the Lovett Building is a great example, a little cavernous but beautifully renovated. Grab a latte and head over to the Book Gallery next door!
Greasy spoon favorite for sliders and fries. Kid-friendly light of day. Late night, the Snow White is where the Brewbaker's crowd lands face-down.
Old Town Snow White Grill, LLC
159 N Loudoun StGreasy spoon favorite for sliders and fries. Kid-friendly light of day. Late night, the Snow White is where the Brewbaker's crowd lands face-down.
The owners started a bakery next door. eM is a great spot for a quiet dinner for two, an upscale dinner with colleagues, etc.
eM
19 East Boscawen StreetThe owners started a bakery next door. eM is a great spot for a quiet dinner for two, an upscale dinner with colleagues, etc.
This is a new-ish restaurant in town. From their website: "Seasonal bites served in a homey, family-owned coffeehouse with outdoor seating & weekly open mikes." That pretty much captures it! The owners are well known for their flagship operation in nearby Strasburg, Cristina's Cafe.
Sexi Mexi Burrito Bar
21 E Boscawen StThis is a new-ish restaurant in town. From their website: "Seasonal bites served in a homey, family-owned coffeehouse with outdoor seating & weekly open mikes." That pretty much captures it! The owners are well known for their flagship operation in nearby Strasburg, Cristina's Cafe.
Starbucks
140A Purcellville Gateway DrFormerly of the green straws. They have a drive-through.
Arts & Culture
Various entertainment in recently renovated downtown theatre space. Everything from live to the occasional burlesque show. Good beer on tap and decent pub food.
28 locals recommend
Bright Box Theater
15 N Loudoun StVarious entertainment in recently renovated downtown theatre space. Everything from live to the occasional burlesque show. Good beer on tap and decent pub food.
Possibly worth admission if you're a history buff. Take a selfie in front of a canon!
23 locals recommend
Washington's Office Museum
32 W Cork StPossibly worth admission if you're a history buff. Take a selfie in front of a canon!
The MSV is really three spaces. There's the museum proper, with Valley dioramas among other neat and kid-friendly exhibits. Then there's the Glen Burnie House and gardens. Must-see for gardeners!
72 locals recommend
Museum of the Shenandoah Valley
901 Amherst StThe MSV is really three spaces. There's the museum proper, with Valley dioramas among other neat and kid-friendly exhibits. Then there's the Glen Burnie House and gardens. Must-see for gardeners!
Educational interactive kid paradise. Three stories tall, recently renovated by local architecture firm Reader & Swartz. The rooftop deck has views of Winchester that are worth the price of admission.
34 locals recommend
Shenandoah Valley Discovery Museum
19 W Cork StEducational interactive kid paradise. Three stories tall, recently renovated by local architecture firm Reader & Swartz. The rooftop deck has views of Winchester that are worth the price of admission.
Patsy Cline grew up in Winchester. The locals have been divided on her legacy ever since. Visit the house, then you decide!
17 locals recommend
Patsy Cline Historic House
608 S Kent StPatsy Cline grew up in Winchester. The locals have been divided on her legacy ever since. Visit the house, then you decide!
Former train station, now renovated into a theatre-in-the-round style theatre. They put on a remarkable number of shows, always topical and current. A great community resource.
8 locals recommend
Winchester Little Theatre
315 W Boscawen StFormer train station, now renovated into a theatre-in-the-round style theatre. They put on a remarkable number of shows, always topical and current. A great community resource.
Drinks & Nightlife
It's just around the corner from the Levi Wickham house, across from the George Washington Office museum. Great beer selection in a well-lighted friendly atmoshere. Last call is midnight!
23 locals recommend
50/50 Taphouse
29 W Cork StIt's just around the corner from the Levi Wickham house, across from the George Washington Office museum. Great beer selection in a well-lighted friendly atmoshere. Last call is midnight!
High energy bar, especially during the summer when the deck's open. Live music many weekend nights, sports projected on the building next door, countless twentysomethings.
27 locals recommend
Piccadilly's Public House & Restaurant
125 East Piccadilly StreetHigh energy bar, especially during the summer when the deck's open. Live music many weekend nights, sports projected on the building next door, countless twentysomethings.
Decent burgers, domestic beer on tap. Pleasant patio scene in daytime. There aren't many places to dance in Winchester. Brewbaker's is one. Noisy sweaty late night destination.
9 locals recommend
Brewbakers Restaurant
168 N Loudoun StDecent burgers, domestic beer on tap. Pleasant patio scene in daytime. There aren't many places to dance in Winchester. Brewbaker's is one. Noisy sweaty late night destination.
This is the latest brewery to open in Winchester. The setting is minimalist. They don't serve food, but you can order in. Oh, and the beer is good.
13 locals recommend
Broken Window Brewing Co.
14 W Boscawen StThis is the latest brewery to open in Winchester. The setting is minimalist. They don't serve food, but you can order in. Oh, and the beer is good.
Another brewery! One of four in Winchester...and counting! The owners are super pleasant. Sit at the bar, and you'll probably meet them. The beer is really good. Try the smoky Chipotle-infused porter. You can take home a can, they'll can you one fresh while you sip.
14 locals recommend
Winchester Brew Works
320 N Cameron St Another brewery! One of four in Winchester...and counting! The owners are super pleasant. Sit at the bar, and you'll probably meet them. The beer is really good. Try the smoky Chipotle-infused porter. You can take home a can, they'll can you one fresh while you sip.
Parks & Nature
Don't let the name fool you. There are no three-headed roosters here! Blandy donated the property, but this is the Virginia State Arboretum. It's a 10 mile drive from Winchester but worth the trip!
24 locals recommend
Blandy Experimental Farm
400 Blandy Farm LnDon't let the name fool you. There are no three-headed roosters here! Blandy donated the property, but this is the Virginia State Arboretum. It's a 10 mile drive from Winchester but worth the trip!
Entertainment & Activities
Eat, drink and watch a movie. Until Winchester gets its own "art house" theatre, this is the place for cinephiles. They also do first-runs. If you need a break from the downtown scene.
29 locals recommend
Alamo Drafthouse Cinema
181 Kernstown Commons BlvdEat, drink and watch a movie. Until Winchester gets its own "art house" theatre, this is the place for cinephiles. They also do first-runs. If you need a break from the downtown scene.
Essentials
Because you never know when you'll need a palette of rice or a $5 rotisserie chicken.
Costco Wholesale
251 Front Royal PikeBecause you never know when you'll need a palette of rice or a $5 rotisserie chicken.
Until we get a WholeFoods (or a Wegman's...or a Trader Joe's), there is Martin's. It's basically a big Giant Foods. The produce is good, if pricey. There are several locations. This is the one closest to the University.
25 locals recommend
Martin's Food
1950 S Pleasant Valley RdUntil we get a WholeFoods (or a Wegman's...or a Trader Joe's), there is Martin's. It's basically a big Giant Foods. The produce is good, if pricey. There are several locations. This is the one closest to the University.
Shopping
Pick up a Frisbee or some kinetic sand. Great destination for parents of young kids, though you might never get them out of there!
Incredible Flying Objects
111 N Loudoun StPick up a Frisbee or some kinetic sand. Great destination for parents of young kids, though you might never get them out of there!
It's that rare thing in the era of Amazon, a bona fide locally owned bookstore. The selection of books is nicely curated, and the staff are super-friendly and eager to help. Great kids section!
Winchester Book Gallery
7 N Loudoun StIt's that rare thing in the era of Amazon, a bona fide locally owned bookstore. The selection of books is nicely curated, and the staff are super-friendly and eager to help. Great kids section!