The Best Restaurants in Winchester, Virginia

Let’s start off our foodie adventures at Cafe del Sol. “Del Sol” means “of the Sun” in Spanish, and this “Cafe of the Sun” is sure to brighten your day and send you rays of warm fuzzies with their fantastic menu of appetizers, soups, salads, panini, pizzas, pastas, sandwiches, wraps, quesadillas, tacos, rice bowls, sides, desserts, beer, wine, and cocktails all in a relaxed yet stylish setting. Whew, that was a mouthful. And in case you thought I messed up when I said “panini,” the plural form of panini is actually panini, not paninis.

Anyway, this Winchester favorite is a must-try. Hmmm, I would say all of the restaurants on this tour are a must-try, actually. Anyway, Cafe Del Sol’s pizzas are probably my favorite with their handmade in-house dough with just the perfect touch of olive oil and sea salt. They bake their yummy pizzas in their brick oven, of course, and their cheeses are whole milk - not that tasteless skim milk stuff. I mean, if you are gonna have some pizza, then have some pizza!

And speaking of pizza, our next two stops are pizza restaurants as well. Let’s get going!

We are coming up on Oak Stone Craft Pizza, and by “craft,” they really do mean craft. This isn’t just your regular old pepperoni pizza place, although you can get a delicious pepperoni pizza here if you really want one. But let’s talk about some of the pizzas that Oak Stone Craft prides itself on creating.

Their Bee’s Knees pizza has white sauce, Brie, Goat cheese, Asiago, apples, sweet onion, rosemary and a drizzle of honey. I wouldn’t even think of combining all those ingredients, but Oak Stone did and WOW is it delicious!

Here’s another crazy combo that will keep you coming back: Their Green Giant pizza has pesto, feta cheese, artichokes, roasted peppers, green peppers, fresh kale and sunflower seeds.
For the meat-eaters out there, one of my favorites is their Carnivore pizza. This hearty pie has natural pepperoni, house meatballs, and local sage sausage.

Now as if delicious craft pizza wasn’t enough, Oak Stone also has a fantastic choice of appetizers that you won’t find at any regular old pizza place. Try out their bacon wrapped meatballs, wood fired brussels sprouts kung pao cauliflower or even their fried pickles. Delicious.

Now let’s talk about cocktails. I think that any restaurant with the word “craft” in its name had better have some amazing cocktails and Oak Stone Craft Pizza does NOT disappoint. With names like Snickerdoodle Swizzle, Stray Hound and Liberace’s Lavender Waistcoat, you know Oak Stone has put a lot of thought and creativity into their cocktail recipes. My personal favorite is the Mango Sombrero - a perfect mix of mango and jalapeno tequila, cilantro, lime and agave.

You can also find a wide array of wine, bourbon, whiskey, scotch and multiple rotating draft beers.

Ok, let’s move on. Our next stop is a trifecta of fantastic restaurants that I can’t wait to show you. Please follow your navigation.

Let’s talk about restaurants on cute, pedestrian streets. Here at the corner of Boscawen and Loudoun is El Centro Restaurant and Water Street Kitchen. To the left down Loudon Street is Roma Old Town Wood Fired Pizza. So, Roma Old Town is a local favorite gathering place here at the walking mall. This casual Italian and Greek restaurant offers hand-crafted pizza, fun appetizers and interesting salads that are sure to make you smile. And as happy as you will be, you can be even MORE happy with a pint of craft beer from Alesation Brewing Company. Their draught beer menu is always changing so you’ll have to check it out for yourself but one of my favorites there has been “Well…Ya Know.” No really. That’s the name of the beer - Well Ya Know. It’s a yummy Belgian Ale. Remember to drink responsibly!

How about we talk about El Centro? This classic Mexican restaurant prides itself in delivering freshness and quality in every delicious bite. Their home-made salsa is off the charts and their carnitas will make you wanna call your mom. You won’t be able to resist ordering something off their margarita menu, since they have 22 different flavors to choose from! Watermelon, mango, passion fruit, coconut and pina colada, just to name a few.

Finally, we have Water Street Kitchen. What will we find here? Down-home cooking by Chef Dan Kalber. His fun take on classic American cuisine will keep you coming back for more. His famous fried green tomatoes are divine, as are the chicken and waffles and the buttermilk brined fried chicken fritters. The Josie grilled cheese and tomato soup will make you feel loved, and if that isn’t enough, their crushed cocktail menu will surely satiate.

You’ve gotta be getting hungry by now. What’s been the most interesting restaurant for you so far? Well, we aren’t done yet, so let’s keep going.

It’s deli time! Since 2013, Aroma Deli has been serving Peruvian Chicken, handcrafted sandwiches and delicious comfort foods. You can even start your day off here with one of Aroma’s breakfast sandwiches or platters.
If you slept through lunch, try out a soft taco or burrito. If you are a huge Peruvian chicken fan, Aroma’s is top-notch. My favorite combo is the half chicken with yucca and plantains. But that’s just me. Get in there and decide what your favorite is!

Wanna dine on some Georgia Fried Chicken while sharing a bucket of boozy Irish Lemonade and listening to your favorite local band? How about dining, drinking and listening from inside a 1900’s grocery warehouse? Yeah? Perfect. Piccadilly Public House and Restaurant is where it’s at. The original brick walls, floors, ceiling and windows will transport you back to the days of simple quality and service that sometimes is lacking these days.
Where else can you get a Bavarian pretzel, a Maryland crab cake, a New York strip, or that Georgia fried chicken? Obviously, there are plenty of beers on tap as well, but they also will serve you up a shot of imported scotch or domestic bourbon. Do you like your shots to have a special twist? Try a Vegas Bomb a Pickle Back shot. It’s always fun to try something new.
With free live music on Friday and Saturday nights, you really should set a date with friends to come back and experience the Piccadilly Public House.

Please pull into the Bonnie Blue parking lot on your left, just before the intersection and listen up. Biscuits and gravy… low country shrimp and grits… peppered beef brisket… pulled pork… fried catfish… fried oysters… southern pimento cheeseburger… sweet corn-jalapeno hush puppies… southern collard greens… What do all of these things have in common? Well, they can all be found in a 1921 Esso Gas Station. Well, at the Bonnie Blue Southern Market and Bakery which is housed in a 1921 Esso Gas Station. You won’t be able to buy gas here anymore but you WILL feel southern charm from the exterior to the interior, to the live music, the patio and the fresh, home-baked goods. Oh, and Bonnie’s is one of the Top 13 BBQ stops from New York to Memphis, according to the New York Times. So, there’s that.

Ok, you can leave the parking lot now, unless you decided to go in and grab a bite. Drive back the way you came in and turn left on Morgan Street. Then follow your navigation. Next up is beer.

And now it’s beer time. We’ve got a brewery up ahead on your left that brews, cans, packages and serves their classic, true-to-style craft beers right here in Winchester. Escutcheon Es-Cutchin Brewing Company is proud of their beers and shows their love to the community with festivals, fundraisers and celebrations. Book your private event here, such as a family reunion, bridal shower or wedding. Or just swing on by for some good old day-drinking.
Escutcheon Brewing Company loves to give tours of their facility. Kids are allowed but dogs are not, so bring little Billy along but please leave Fido at home.
Escutcheon doesn’t serve food inside the brewery but they are totally cool with you bringing your own food in. Sometimes they’ll even have food trucks parked outside to make that even easier. Follow your navigation until we get to the Caribbean. Yes, the Caribbean.

A Caribbean restaurant in Winchester, Virginia? You’d better believe it. It’s right here in the shopping plaza diagonally to your left. Winchester may not look like the Bahamas, Costa Rica or Jamaica, but the cuisine at Island Delights Caribbean Restaurant is sure to take your tastebuds back to soothing sunshine and warm island breezes. Obviously the most popular dish here is the Jerk Chicken, which is freshly grilled outside daily, but the curry chicken and pepper steak are tied at a close second. There’s just something about the appetizers and desserts that make me happy though. I like to pregame with the fried dumplings and wrap it all up with either their rum cake or potato pudding.
If you are feeling a little adventurous, the beef feet are actually pretty dang good. Sometimes it’s nice to “step” out of your comfort zone. See what I did there? “Beef feet”, “step out?” Too soon? Ok. My apologies.
As for drinks at Island Delights, they have a fully stocked bar, plus a really run selection of authentic Jamaican sodas. Transform your day in a Caribbean way!
And that wraps up our tour.
Feel free to stop in any of the restaurants we discussed on this tour, I bet you’re hungry listening to me talk about food this whole tour. If you’d rather see more of the Winchester area, make sure to give Brandon a call at 703-727-5890 or send him an email at bcurtis@weichert.com.