When you’re in the Shenandoah Valley, every breath you take brings you closer to a natural, calm state. As you drive through the winding roads, you end up at your destination: Winchester, VA.
The area’s natural surroundings give fruit to tons of fresh produce, rich grains, and organic meats — and paired with the expertise of Mideastern chefs? Winchester is a top spot for comfort food and delectable American cuisine.
Here at Blue Maple, we’ve welcomed thousands of guests like you to our 80 luxurious vacation rentals in the valley. And when guests get hungry, we come in hot with our local recommendations. Keep reading for the best restaurants in Winchester!œ
1. Village Square Restaurant
- Website: villagesquarerestaurant.com
- Price point: $$$
- Address: 103 North Loudoun Street, Winchester, VA
- Favorite menu items: Butternut Squash Ravioli, Steamed Crab
- Type: Elevated American Cuisine
Craving a rich quiche or Angus beef burger? Elevate your taste buds with the Village Square’s upscale take on classic American cuisine in Old Town Winchester. No matter how discriminating your group, this joint has something delectable for everyone. They also have a playful array of seafood dishes, like North Carolina Shrimp and Scallops, crab cakes, and a wide selection of oysters.
But maybe you had plans to BBQ this evening on the deck at our Tall Peak Chalet. In that case, opt for the Raw Bar Menu. Who can say no to freshly shucked oysters with caviar or a rich Rockefeller with bacon and cheese? Order a bottle of Chardonnay for the lady, or indulge in a bourbon on ice from the restaurant’s hand-picked private barrels.
2. Antica Trattoria
- Website: anticatrattoriarestaurant.com
- Price point: $$$
- Address: 25 S Indian Alley, Winchester, VA
- Type: Italian cuisine
- Favorite menu items: Abundant ravioli options, risotto al pescatore
Italian beer and pasta aficionados unite at this Downtown Winchester spot for home-cooked, comforting fare. Antica Trattoria isn’t easy to spot as a first-timer, but you’ll find it tucked along Indian Alley. Once you’re in, indulge your heart and appetite with meat-stuffed rice balls from Sicily or endless stuffed ravioli options (lobster, ricotta, mushrooms, you name it).
And if you’re looking for a lighter-carb option? Antica’s got you covered with a ton of veggie- and protein-rich dishes. Start with an oh-so-fresh caprese salad and dig your chops into a lemon-dressed veal cutlet or mushroom-covered filet mignon. Buonissimi!
Quick note: Violino Ristorante Italiano is another favorite for creamy-sauced pasta and classic Italian eats!
3. Big L’s Bagels
- Website: wincfood.com/eat/big-ls-bagels/start
- Price point: $
- Address: 38 E Piccadilly St, Winchester, VA
- Type: Bagels
- Favorite menu items: Dr. P (smoked salmon + cream cheese), Braided Bagels
Craving a quick bite before you hike through Shenandoah River State Park? Or perhaps you just finished seeing a landmark like the Patsy Cline Historic House and want a snack before heading home.
Big L’s Bagel takes the cake for Winchester’s best bagels — we’re talking homemade and rich with toppings. How does high-grade smoked salmon, milky cream cheese, and satisfying avocado sound? We’ll take two for the road. You can also buy a bunch of bagels via takeout and customize them at home or save them for breakfast the next day.
A nice bonus? These guys know their coffee. Any Italian would chin-chin to their espresso, and as for us, less traditional sippers? Go for the caramel latte — seriously, its smooth flavor and satisfying sweetness eliminate the rest of your stress for the day.
4. Bonnie Blue Southern Market & Bakery
- Website: winchestersbestbbq.com
- Price point: $$
- Address: 334 W Boscawen St, Winchester, VA
- Type: Southern food
- Favorite menu items: Fried chicken, Pancakes, Shrimp & Grits
Carolina native Brian Pellatt brought southern cuisine up to Virginia in an Esso gas station back in 2012 when he opened Bonnie Blue. These days, Bonnie Blue stands tall in its blue-painted abode, welcoming visitors to its drool worthy Southern fare.
Craving fresh biscuits like grandma used to make? How about a Louisiana po’boy or Charleston pimento cheeseburger? You name it and they probably have it if it’s from down south — and they’ll serve it to you on a diner booth or patio, whichever you’d like!
Keep in mind that this is primarily a brunch/lunch spot. Bonnie Blue closes at 6 p.m. most days and even earlier at 4 p.m. on the weekends. And if you head there on a Friday, go on early for the joint’s early dinner special — a three-courser, complete with your choice of hush puppies, burnt ends, or wings as a starter, amongst others.
As for the main course, pick from a Shenandoah beef ribeye, steelhead salmon filet, or heritage pork loin. All Friday dinner specials come with an autumn pie dessert, too!
5. Cork Street Tavern
- Website: corkstreettavern.com
- Address: 8 W Cork St, Winchester, VA
- Price point: $
- Type: Pub food and craft beer
- Favorite menu item: Ribs, Fried Chicken, and Mozzarella Sticks
Visiting on a windy Fall weekend? Come warm up with good food and a beer by the fireplace at the Cork Street Tavern! Here, you’ll find craft beers galore, from traditional PBRs to tart cranberry ciders. An exceptionally delicious seasonal choice is the Gingerbread Stout, infused with wildflower honey and ginger — so smooth! Can’t choose? Neither could we — that’s why we opt for the $10 flight every time we visit.
The tavern isn’t fancy, but the food packs a punch of comfort and flavor. Entrees are hearty and mouthwatering, like the Nashville fried chicken or baby back ribs. You’ll also find some seafood options, like salmon marinated in sweet honey Bourbon sauce or southern fried catfish.
Another honorable mention for pubs? The Union Jack Pub is a classic over on N Loudoun St.
6. Piccadilly’s Public House & Restaurant
- Website: piccadillypublichouse.com
- Price point: $$
- Address: 125 E Piccadilly St, Winchester, VA
- Type: Brewpub/Taphouse
- Favorite menu item: Louisiana Pulled Pork, Nachos
Set in a historic warehouse, Piccadilly’s caters to those seeking live music, meat entrees, and a touch of grandeur with its event-friendly Winchester Room.
From live DJs to folk music, live entertainment is varied and abundant, and you can enjoy it every Friday or Saturday Night. Food-wise, you can pick from indulgent Louisiana pulled pork, New York Striploin, or Georgia Fried Chicken, amongst countless salads and appetizers to prepare the palate.
Not sure if you could bring the kiddos? Please do — the joint is superbly kid-friendly, especially during the lunch hour. We also commend Piccadilly’s for their unwavering commitment to stellar customer service. The staff is always eager to make your visit memorable and caters to your every need.
7. Uno Pizzeria & Grill
- Website: restaurants.unos.com
- Address: 103 E Piccadilly St, Winchester, VA
- Price point: $$
- Type: Chicago Deep Dish Pizza
- Favorite Menu Items: Classic Chicago Deep Dish with Sausage
Traveling from the Windy City? Enjoy a slice of home with a trip to Uno, a well-loved pizza joint serving up decadent deep dish varieties, like the Meatball Ricotta, Prima Pepperoni, or classic Chicago with lots of juicy sausage chunks.
And if you’re not in the mood for such a rich meal? You can enjoy a thin-crust option too; don’t worry. We also love Uno’s light Mediterranean Chicken Dish, Sirloin Steaks, and fresh salads! This place has operated since 1943, so rest assured you’re dealing with the best experts in deep dish!
Unleash Your Inner Foodie in Winchester with Blue Maple!
Winchester gifts you with ample dining experiences to write home about, from freshly caught fish to comforting American classics. For a small town of just under 30,000 people, the locals sure know how to appeal to everyone’s taste buds.
And once you’re stuffed from your heaping deli sandwich or Italian pasta bonanza? You’ll want a cozy abode to unwind and enjoy your vacation with your loved ones. Blue Maple offers you a variety of cabins and chalets in the Winchester area, complete with amenities like hot tubs, quick WiFi, firepits, and a mix of entertainment options.
Ready for a vacation your heart (and stomach) will remember forever? Book your Winchester stay today!