17 Cant-Miss Best Restaurants in Winchester Virginia

Apart from the many known restaurants in Winchester, this city is a world in itself that is waiting to be experienced and explored.

While its many scenic parks beckon adventurer and nature lovers, its many pretty lakes, spectacular museums, and myriad activities are what make this city to be unique.

Its undeniable hospitality and old-world charm are a sure shot for every fun-seekers. However, foodies can also rejoice as there are a plethora of restaurants in Winchester to eat from.

The restaurants in Winchester, VA, bring not just traditional delicacies but also the best of world cuisine to every guest’s plate.

So, what are you waiting for? Absolutely, there should be nothing!

Restaurants in Winchester VA

1. Violino Ristorante Italiano

The Violino Ristorante Italiano is one of the finest, casual & famous restaurants in Winchester. It has been serving authentic Italian lunch and dinner in this downtown for nearly three decades.

Apart from its great calamari, Galleto al Limone, and bread to enjoy, you’ll literally get thrilled with the excellent service and warm welcome.

More so, the mussels, pasta, and various seafood options on the menu list are equally great and look so scrumptious and appealing.

The luncheon special with shrimp, zucchini, and cheese is equally a perfect combination for a birthday celebration or a get-together.

Best part, the food quality at Violino Ristorante Italiano is always stellar, and the portion is extreme to the value.

Even at that, the staff is very attentive and so friendly. Everyone genuinely enjoys their job. You can definitely tell this establishment values its employees!

To top that up, the decor makes you feel like you’re in Italy, and the service, from start to finish, was top-notch. If you’re in Winchester and you’re looking for an old-school feel and personalized service, this is the spot to be!

Address: 181 N Loudoun St, Winchester, VA 22601, United States

2. Village Square Restaurant

The Village Square Restaurant is a new American dining joint with a full bar in the rustic and intimate environs of a historic building.

It is popular among guests and has organic food varieties. The chophouse salad here is always fresh. Also, they do fry the goujons to perfection, and aside from being perfectly seasoned, the preserved lemon tartar sauce that accompanies it is just the best you’ll get in Winchester.

Steaks, scallops, and monkfish are also a big hit. Although, I’ll suggest you stay away from the gnocchi unless you like very creamy sauce!

You can also splurge on the chocolate torte. It’s a whole experience you should not miss!

The wild mushroom sauce with steaks is equally a great pairing with the Chalk Hill Pinot noir, and if you’re willing to try out other dishes, be sure to have a plate of salad or quiche.

Most admirably, the menu and its ingredients rotate based on the season. So, whether you’re around during the summertime or winter period, you can’t be short of the perfect bit.

Are you still scouting out multiple restaurants in Winchester? Stop the search! This is an option to beat! They have an appetizer, entree, lunch, and dessert, with unlimited champagne. You’ll love everything here!

The customer service is also phenomenal, the food is outstanding, and Chef Dan really makes sure you have a fantastic experience.

Visit Village Square Restaurant from 11:30 am – 9:00 am on Monday through Saturday and on Sunday from 11:30 am to 2:30 pm.

Address: 103 N Loudoun St, Winchester, VA 22601, United States

3. Uncle Julio’s

Uncle Julio’s is a Tex-Mex chain restaurant in Helen that serves mesquite-grilled fare & margarita-sangria swirls in a hacienda-style space.

Featuring an open kitchen setting, Uncle Julio’s is one of the best Western restaurants in Winchester that brings authentic Western cruising to Virginia.

Immediately you arrive here, you’ll have access to some free chips and salsa, so be careful not to overfill yourself before the main meal.

Afterward, you can make your order from the variety of available meals, including pancakes, cheese, guacamole, and more. Best of it all, there’s also a plethora of healthy and vegetarian options. It includes fresh juices, açaí bowls, among others.

Unlike many other restaurants in Winchester, after breakfast here, the menu becomes more health-focused, with lots of other specials and creative options.

Overall, Uncle Julio’s is a place to be if you want some classical dining experience while being away from your city!

Plan a visit to this restaurant from morning through down.

Address: 13920 Promenade Commons St, Gainesville, VA 20155

4. Union Jack Pub & Restaurant

Winchester is one of those beautiful cities in the States that gets the food scene right, and the Union Jack Pub & Restaurant is no exception!

Union Jack Pub & Restaurant is an excellent place for lunch, breakfast, and dinner. In fact, it’s also one of the best brunch spots you can think of in Virginia.

More so, this underground restaurant has a standard pub with great beverages and top-notch live music.

The building itself is gorgeous, with exposed high ceils and brick, with massively plush beautiful curtains everywhere.

This restaurant has a genuine that marks a successful combination if you’re in town.

Savor decadent beverages, delectable food, and top-notch live music against the backdrop of a funky, eclectic, yet exquisite art venue!

It’s simply one of the best restaurants in Winchester; it wouldn’t be anything short of memories here!

Address: 101 N Loudoun St, Winchester, VA 22601, United States

5. SabaiThaiWinchester Restaurant

SabaiThaiWinchester Restaurant is a chef-owned restaurant located at Loudoun Street in Winchester, Virginia.

This eatery serves American, Canadian, and other international cuisines with a core emphasis on fresh local ingredients.

Ever since it has been around, it has been regarded as one of the best restaurants in Winchester because of its uniqueness. It’s so popular among locals that every lunchtime is filled with guests.

Beyond that, the ambiance in this restaurant is rustic and inviting. In fact, the menu here changes daily based on the farmers, products, and foragers.

And to top that up, the dishes in this beautiful restaurant are often prepared in their wood-fired oven or over an open wood-fired grill.

From scrumptious appetizers to Halibut filets to its various sandwiches, you can’t go wrong visiting this restaurant.

Santa Fe bowl with tasty Salmon, chef’s salad with roared chicken breast, and Duck breast are also popular demands here.

You can also try its seared sea scallops, citrus-marinated swordfish, or some portion of fried shrimp for seafood.

Me, my favorite is their chicken enchiladas, but the marinated squid and Roasted pork loin are also superb!

What is more, the bar zone is so large, with a great happy hour menu that’ll satisfy your cravings. The signature cocktails are refreshing, and the wine list is pervasive!

Plan a visit on Sundays – Saturdays from 11 am – 10 pm.

Address: 24 S Loudoun St, Winchester, VA 22601, United States

6. Antica Trattoria

If you’re looking for some classic Italian restaurants in Winchester, Antica Trattoria is the best option worth considering!

This restaurant’s interior and exterior are Italian-themed, making it look highly authentic and so welcoming.

Immediately you walk inside, with its gorgeous look, you will realize that you have stepped back in time. In each of the dining rooms here, you’ll enjoy a different vibe and cozy setting.

At the Antica Trattoria, the menu consists of plenty of dining options, including that vegetarian, vegan-free, and gluten options. So, there’s something for everyone to eat in this lovely restaurant.

Most Interestingly, the prices of meals in this place are equally reasonable for both the taste, the portion, and the quality; hence, you know you’re getting some great deals at fair prices.

If nothing more, be sure to order the lasagna. It does come with a plate of cannoli, Italian sausage, and some portion of lasagna will do as well!

Also, don’t miss out on the rolls and salad, and if you enjoy seafood, get yourself the Crawfish Julienne; it wouldn’t disappoint you!

Sumptuous food, excellent service, and, most importantly, better drinking straws. They’re firm and won’t fail you during any dinner hangout!

Besides, they equally allow guests to bring their personal drinks for a reasonable fee, which is great!

Visit Antica Trattoria from Tuesday through Sunday from morning to evening.

Address: 25 S Indian Alley, Winchester, VA 22601, United States

7. T- Bones Bar and Grill

If you’re looking for a great place in Winchester for Barbecue and roasted chicken, then you have to give T- Bones Bar and Grill a try!

Located at Kent Avenue in downtown Winchester, the T- Bones Bar and Grill prides itself on its fantastic quick bites, Western cuisine, and lovely ambiance.

This ambiance is both comfortable and industrial, perfect for a date night, hanging out, or grabbing a weekend brunch.

Beside Barbecue, other items on the menu list include a sandwich with fries and chips that comes crunchy and hot. Turkey, Brisket, and pork are also better options here; they’re sauced and seasoned very well. Not only that, a spicy margarita is also a great combination of spicy and sweet.

Although it may be hectic in there, that isn’t an issue! They’re used to it, and everything seemed to run without a hitch, and unlike other restaurants in Winchester, the waiting period here is so bearable.

Customer service is equally an impressive attribute of this restaurant. Notwithstanding this is a self-serve restaurant, the employees will frequently come around to you and wouldn’t mind offering refills at intervals.

If plentiful and cheap dishes is your priority, you can check other restaurants in Winchester, but if you don’t mind paying something higher for quality dishes, T- Bones Bar and Grill is a place to be!

Plan a visit to T- Bones Bar and Grill from Mondays – Thursdays, 11 am – 10 pm, and Fridays through Saturdays from 11 am – 1 am.

Address: 567 N Kent St, Winchester, VA 22601, United States

Planning a trip to Virginia Beach? Check out some of our top best restaurants in Virginia Beach to dine at!

8. Water Street Kitchen

The Water Street Kitchen is a cozy restaurant with patio tables and a full bar offering modern American fare & live music.

It’s a quaint destination that provides an intimate and casual neighborhood atmosphere, making it one of the best restaurants to eat while in Winchester, Virginia.

In this iconic spot, you’ll see diverse contemporary American selections, including Gyro, which appears so tender and packed with lots of flavors. If that will not be enough, the veggie burger or a plate of falafel is also worth dying for.

For appetizers, salads, and sandwiches are made available all throughout the day. If you want something more, I also recommend a plate of crab cakes; it will not take long enough for you even have a photograph before it is served!

Above that, the chef’s entrees in this restaurant are creatively prepared all days of the week.

Whether dining for pleasure or planning to host a party or having an upcoming family event, meals at Water Street Kitchen will surely make a lasting impression!

Note, there’s equally a patio dining with daily drink offers. It features seasonal flowers, ornamental plants, and herbs, making it a perfect place to watch the sunset.

Although parking may be so tricky here, so, I advise you to park at the nearby garage that is just a walking distance away!

Address: 2 S Loudoun St, Winchester, VA 22601, United States

9. Papermill Place

Known for its traditional American comfort dishes are the draw at this down-home establishment with patio seating.

At Papermill Place, its commitment to producing sustainable traditional dishes doesn’t go without being noticed!

From its iconic options of Buffalo chicken pizza to its series of local offerings and lots of Lemon chicken soups, there’s no match for this restaurant in Winchester.

Another lovely attribute of this restaurant is the price fixed on each menu item. With significant portions and well-cooked foods, so many visitors traveling to Winchester are always conscious of not missing the opportunity to eat at Papermill Place.

One more thing that I cherish about this restaurant is the conduct of its staff. All staff that works here understands the nature of their job. Therefore, you can tell the food was actually cooked with love!

However, beforehand, I suggest that you should check their changing menu options, this is because takeout is always of.

You can plan a visit to Papermill Place on Mondays through Sundays from 6 am to 2:00 pm.

Address: 2214 Papermill Rd, Winchester, VA 22601, United States

10. Piccadilly’s Public House & Restaurant

If you can’t have an enjoyable meal without a drink by your side, Piccadilly’s Public House & Restaurant is definitely for you!

From its gorgeous landscape design to its rustic dining area, Piccadilly’s Public House & Restaurant is one of the best restaurants in Winchester!

Speaking of its menu, Piccadilly’s Public House & Restaurant offers bison, Mac & Cheese, papaya salad, fresh Salad roll, sushi, fried calamari, and more.

They equally offer salmon burgers, fried clams, catfish, chips, and chicken strips (freshly made) with key lime pie, cheese dip, and a long list of menus that’ll make you more satisfied.

Additionally, for the best seafood options, you’ll have nothing to regret in this place. They are a great illustration of what Winchester food is at its core; all things in this restaurant are always great!

After dining, you don’t need to be in a hurry to leave; the outdoor garden that surrounds this restaurant is lovely to behold, and it will surely be worth your time!

Anything more? This restaurant is kid-friendly on the patio. Thus, you can also plan a visit with your kids while also coming with your four-legged friend!

Visit Piccadilly’s Public House & Restaurant on Tuesdays through Thursdays from 11:30 AM – 10 pm. On Fridays and Saturdays, this restaurant opens at 11:30 AM and closes at 1 pm. If you are here on Sunday, you can come between 11:30 PM – 1:00 PM.

Address: 125 E Piccadilly St, Winchester, VA 22601, United States

11. Cork Street Tavern

The Cork Street Tavern has all the great deals, and on all days, it’s ready to end your hunger!

From their delicious breakfast to their enjoyable lunch and dinner, the Cork Street Tavern has lots of bites to offer for whatever meal you’ll love to fill.

You can never go wrong with anything on the menu list! The salsas are homemade, the tortillas are so yummy, and the fajitas with beans with the chicken burrito are also great options!

I equally recommend their Mexican soups, not just because it is always flavorful but because it feels so nourishing all the time.

Unlike all other restaurants in Winchester, the menu here is overly complex; there are spicy foods, and vegan and gluten-free options, which would be a great deal if you don’t fancy seafood options.

Besides, this great restaurant has an amazing staff who have to indebt understanding of the menu and as well give perfect drink pairs for every meal.

Cork Street Tavern is obviously one of the best options for dining in Winchester.

Meanwhile, if you are here, I suggest you come during the weekend if you detest crowds because it’s somewhat crowdy during the week.

Whichever way, this restaurant opens at 11:00 AM and closes at 12:00 AM.

Address: 8 W Cork St, Winchester, VA 22601, United States

12. El Centro

El Centro is a casual restaurant in Winchester offering a variety of traditional Mexican dishes in a colorful interior.

Being one of the famous restaurants in Winchester that have been portraying the high-end dining experience for everyone for several decades, this restaurant receives over one million guests annually.

It consistently creates a world-class experience and has been maintaining its innovation while equally reflecting so much on the traditional American menu.

Moreover, this restaurant also respects Winchester’s past with its sturdy construction and posh décor. And, other than its traditional soups and meals that it’s known for, El Centro also offers Cocos with lots of flavorful Cuban staples and stuffed potatoes.

In addition, this restaurant adopts fresh ingredients that are locally sourced (though few items are flown in).

This is simply a perfect restaurant in Winchester, Virginia, to grab lunch, dinner, or anything in between, with absolutely zero worries about accommodating the little ones, too.

Whatever you’ll get here, don’t forget also to try the desserts; it is what you’ll love!

Impressively, there is no long wait time here, so it’s equally the best option if you need to get your food as quickly as possible. Nevertheless, if you’re picking up, come at least 30 – 40 minutes ahead so that you can quickly place your order as soon as you’re here.

Plan to visit El Centro daily from 11:30 am through the evening period.

Address: 1 N Loudoun St, Winchester, VA 22601, United States

13. Glory Days Grill

The Glory Days Grill is a relaxed environment in Winchester that offers American comfort staples and take-out options. It’s every local’s favorite and a beautiful, well-kept restaurant that has been serving various delicacies for several decades back.

More so, it has a large bar, the dining room is so cozy and welcoming, and the outdoor area is also always fabulous every evening.

In this restaurant, you’ll see everything from cheese to shrimp to mac and oysters. In fact, crab cakes, sweet pieces of bread, calamari, and numerous steaks are among the top picks here.

The dinner options here also have a perfect list that will give you the proper hangout vibe and the cocktail menu is as perfect as anything you’ll want.

Additionally, for any kind of special outing, you can make a reservation for an inviting room. It will surely make an excellent deal for such an exclusive gathering!

Amazingly, this cozy spot not only tempts guests with its charms but with a menu list that is filled with the best flavors.

It will surely be a great deal to be here if you’re looking out to pick from the best restaurants in Winchester, Virginia!

Plan to check out Glory Days Grill Bar every day from 11 am to 5 pm.

Address: 130 Featherbed Ln, Winchester, VA 22601, United States

14. Kasbah Spanish Moroccan Tapas Restaurant

If you’re in Winchester and need Spanish and Moroccan tapas, you can’t go wrong visiting Kasbah Spanish Moroccan Tapas Restaurant!

Located along the historic Loudoun Street, the Kasbah Spanish Moroccan Tapas Restaurant is a contemporary African and Asian restaurant with an industrial-chic vibe.

The Steakhouse is one of the best restaurants of its kind in Winchester, with diverse menu options at relatively low prices.

On its extensive menu, there are creative selections of Moroccan alongside contemporary offerings, including banker’s shrimp tacos that are served with ponzu sauce. All are always cooked to perfection, and you’ll love it.

Their sushi & standard menu equally offer diverse options that will satisfy any dietary restriction and preferences.

So, this is not a restaurant you will want to squeeze into your schedule; obviously, there is something for everyone here!

Best of it all, this restaurant also features extensive wine options. Hence, you wouldn’t find it challenging to get the perfect pair for whatever order!

Address: 158 N Loudoun St, Winchester, VA 22601, United States

15. Olive Garden Italian Restaurant

Olive Garden Italian Restaurant has some of the best Italian dishes in Winchester, and it’s a perfect head-out for anyone looking to have a quick bite while in Virginia.

They are known for grilled beef & other Italian dishes in a unique ranch-style space that is so welcoming.

Although it is not a big joint, they have the best extensive menu with perfect combinations that will make it highly customizable for you!

From their lobster Mac & cheese to their chicken tenders with fries to lots of Melissa sauced the Olive Garden Italian Restaurant is a must-stop if you’re in Winchester.

And if you want something more, I recommend you place an order for a portion of baked hamburger, potato, or filet mignon. They are always cooked to perfection.

The food tastes delicious, is always prepared right with good size portions, and the staff acts so courteously, just like what you will expect from a classic restaurant domiciled in Italy!

In fact, they also have a wide range of growers, wines, beers, and ciders that match their different menu options.

Olive Garden Italian Restaurant is definitely a great option for the best restaurant in Winchester if you’re looking for a fancy option!

This is ready to serve your meals from 11:00 AM to 10:00 PM.

Address: 2590 S Pleasant Valley Rd, Winchester, VA 22601, United States

16. Sbarro

Up next is Sbarro. This polished, comfortable restaurant offers pizzas and other traditional American dishes.

They prefer using locally sourced ingredients and always have the freshest menu. Aside from pizzas, you will find comfort dishes like Ruben salmon, Pastrami, and shrimp dishes; chicken sandwiches will never disappoint you!

You can as well try something different, like fried cheese grits, pulled pork nachos, or a little portion of arugula and potatoes. Everything on the plate balances each other nicely, and they’re all fantastically cooked!

They also offer brisket tacos, cakes, platters, tomato bisque, and even a few fried pickles choices.

Do not forget to wash it all down with their local wines or juice; if you want it so differently, a portion of the homemade pie will be worth it!

Although, unlike other restaurants in Winchester, the menu here may appear so little, as it is, it is devoid of any form of obnoxiousness.

Note there’s no need to make a reservation. Nonetheless, they do ask if you plan to come to a big party. Thus, if that is the case, put a call through to them ahead of time so they can know.

Make plans to be here before sunset so you can get a better seat to catch the sun while it’s going down.

Address: 1850 Apple Blossom Dr, Winchester, VA 22601, United States

17. North Central Va Restaurants

Eating a meal at North Central Va Restaurants is sure to be loved at any bite, as this eatery serves lip-smacking dishes day after day.

It opened in 1992 and has since been the awesome standard of elegant dining in Winchester. The food, the interior, and the service at North Central Va Restaurants are the height of opulence.

They have staples such as Redfish, shrimp with plenty of bone marrow, and Amberjack. Their burgers are also fantastic for lunch, and brunch options are equally available on weekdays.

More so, the cocktails are as well crafted to perfection, and the fried chicken is just what you’ll want.

For an appetizer, a plate of fried bacon or okra will do, and grouper or swordfish will be the best pair for the entrée.

If you don’t want anything more, I recommend you place an order for some Duck breasts. It’s always yummy and perfectly cooked. Besides, it’s tender, and the sweet sauce is paired well with it.

More particularly, the swordfish steak is always flavorful, and it’s always with the perfect vegetable orchestra of umami!

Winchester is so lucky to have this culinary adventure! No doubt, it’s of the best restaurants in Winchester! Don’t miss out if you’re near this downtown.

Plan a visit to North Central Va Restaurants from Mondays – Thursdays between 11 am – 11:30 am. Fridays to Saturdays, 11 am – 1:30 am, and Sundays from 11 am – 11:30 pm.

Address: 2227 Valley Ave, Winchester, VA 22601, United States

Final Remarks

So, what’s delaying your travel to Winchester? Obviously, there should be nothing!

Don’t forget to come hungry; it’s going to be fun and exciting!

Bon Appetit!