By Kaitlin Hill  |  Photos by Callie Broaddus

Whether you call Middleburg home, it’s your favorite escape, or you are visiting for the first time, it’s easy to fall in love with the town’s charm. The tree-lined main street is home to unique shops, friendly faces and fantastic food. Though our town may be small, with a population hovering just under 700, it has a huge food scene that is a mix of longtime family favorites and not-to-be-missed newcomers.

Explore Washington Street or saunter down a side street on Middleburg’s main drag, and you can find anything you are craving. From cozy coffee nooks to authentic Thai food and everything in between, Middleburg has it all. The choices may seem overwhelming, but don’t worry. For our 35th Anniversary Issue, we’ve done some of the work for you, highlighting the best of downtown Middleburg’s food and beverage offerings and where you can get them.

Cuppa Giddy Up

8 E Washington Street (p): 540 687 8122

Hours: Monday – Thursday: 7:00am to 5:30pm, Friday & Saturday: 7:00am to 6:00pm, Sunday – 7:00am to 5:00pm

Cuppa Giddy Up

Cuppa Giddy Up

Start your morning with your favorite pick-me-up or one of Leslie’s many specialty drinks. Her decadent Raspberry Mocha Dream is not to be missed. Sweet, lush and expertly brewed with the perfect amount of froth on top. Pair it a poppy seed bagel (Leslie buys fresh from Ashburn Bagel Shop), and nestle into one of the shop’s squashy chairs for a tranquil morning of excellent coffee and the chance to catch up on Middleburg happenings. Leslie’s place has all the papers at your disposal and the constant coming and going of local regulars.

Julien’s Café

3 W Washington Street (p): 540 687 3123

Hours: Friday – Tuesday: 11:00am to 9:00pm, Wednesday – Thursday: closed

Juliens Cafe

Julien’s Cafe

Stop in to Julien’s Café for a taste of France for lunch or dinner. Frainçoise, the shop’s proprietor, recommends the Chicken Delaney. The exquisitely cooked chicken breast is stuffed with sweet dates and creamy goat cheese. The dish is served with mashed potatoes and seasonal vegetables and blanketed in rich gravy. What’s more, this indulgent dish is gluten-free.

Red Fox Inn & Tavern

2 East Washington Street (p): 540 687 6301

Hours: Monday – Friday: 8:00am – 10:00am (Breakfast) and 5:00pm – 9:00pm (Dinner), Saturday: 11:30am – 2:30pm (Champagne Brunch) and 5:00pm – 9:00pm (Dinner), Sunday: 11:30am – 2:30pm (Champagne Brunch) and 5:00pm – 8:00pm (Dinner)

Red Fox Inn

Red Fox Inn

This historic Middleburg staple has welcomed guests since 1728. Nearly 300 years later, the Red Fox family still offers impeccable service in addition to new and exciting dining experiences. Treat yourself to the four-course Game and Seafood Tasting. This tour of Virginia’s finest seasonal and local ingredients ends with a Port Poached Pear. Dressed with Earl Grey crème anglaise and hazelnuts, it is the perfect finish to a night of elegant dining.

Red Bar Sushi

16 E Washington Street (p): 540 326 8900

Hours: Monday – Thursday: 11:30am – 2:30pm (Lunch) & 4:30pm – 9:00pm (Dinner), Friday: 11:30am – 2:30pm (Lunch) & 4:30pm – 10:00pm (Dinner), Saturday: 12:00pm – 10:00pm, Sunday: 12:00pm – 8:30pm

Red Bar Sushi

Red Bar Sushi

Red Bar Sushi may be new in town, but they are offering up big flavors as Middleburg’s only sushi joint. The Chef’s Sashimi Omakase includes a bounty of fresh seafood, hand-picked by the chef each day. Pair it with a refreshing Soju-tini for a delightful meal in a fun atmosphere.

Side Saddle Café

7 W Washington Street (p): 703 300 5765

Hours: Wednesday: 11:00am – 4:00pm, Thursday: 11:00am – 4:00pm and 4:30pm – 8:00pm (Happy Hour), Friday – Saturday: 9:00am – 8:00pm (Live Music 6:00pm – 8:00pm), Sunday: 10:00am – 4:00pm (Live Music from 1:00pm – 3:00pm), Monday and Tuesday: Closed

Sidesaddle Cafe

Side Saddle Cafe

The Side Saddle Café is a must for cozy breakfasts with wholesome ingredients. Try the FOA Famous Waffles, topped with fresh organic berries and a generous dusting of powdered sugar. The light and fluffy waffles are an old family recipe, adapted to be gluten-free. Be sure to get a side of bacon or sausage from their Fields of Athenry Farm.

Teddy’s Brooklyn Pizza

9 E Federal Street (p): 540 687 8880

Hours: Monday – Thursday: 11:00am – 9:00pm, Friday – Saturday: 11:00am – 10:00pm, Sunday: Closed



Check out Teddy’s for a taste of authentic New York pizza right in Middleburg. Their secret recipe has been in the family for decades and is all about the perfect crust. Grab a slice of classic cheese pizza and see for yourself. And if you’re up for dessert, you have two options: “one cannoli or two.”

Middleburg Common Grounds

114 W Washington Street (p): 540 687 7065

Hours: Monday – Friday: 6:00am – 6:00pm, Saturday – Sunday: 7:00am – 6:00pm

Common Grounds

Common Grounds

In addition to expertly prepared coffee and tea, Middleburg Common Grounds offers a long lunch list. If you’re health minded, you can make any of their tempting sandwiches into a salad. Try the “Madison” on a bed of greens. It’s overflowing with imported Italian tuna, Tuscan white beans and Kalamata olives.

Red Horse Tavern

118 W Washington Street (p): 540 687 6443

Hours: Monday – Sunday: 11:00am – 10:00pm

Red Horse Tavern

Red Horse Tavern

The Red Horse Tavern’s menu has something for everyone with an array of tasty appetizers, loaded salads and stacked burgers. Though, if you ask the restaurant owner Sam, he’ll tell you to order the fish tacos. They are loaded with fresh cod, cheese and veggies and come with a side of house-made tortilla chips and salsa. Enjoy them outside on the spacious patio.

Middleburg Deli

2 N Liberty Street (p): 540 687 3456

Hours: Monday – Saturday: 10:00am – 6:00pm, Sunday: Closed

Middleburg Deli

Middleburg Deli

Come hungry to Middleburg deli for one of their overloaded sandwiches. The manager, Maria, will customize a sandwich for you or whip up their famous Little Italy. This huge sub is layered with Mortadella, pepperoni, Genoa salami, provolone cheese and veggies. Take a bite, and you’ll see why they call it the “Best in Loudoun County.”

Best Thai Kitchen

4 E Federal Street (p): 540 326 8111

Hours: Monday – Sunday: 11:00am – 9:00pm

At Best Thai Kitchen you’ll find bona fide Thai Food cooked as owner Jamie and her chef sister grew up eating it. Jamie buys most of the ingredients straight from Thailand, insisting on highest quality. The Pad Thai, made with rice noodles, sprouts, spring onions and shrimp, is tossed in a sweet and tangy tamarind-based sauce that is heavenly.

King Street Oyster Bar

1 E Washington Street (p): 540 883 3156

Hours: Monday – Thursday: 11:00am – 9:30pm, Friday – Saturday: 11:00am to 11:00pm, Sunday: 10:30am – 9:30pm

King Street Oyster Bar

King Street Oyster Bar

Head to King Street Oyster Bar for the freshest oysters in town. At their raw bar, they offer both East and West Coast varieties by the half-dozen or dozen. If you’re looking to eat local, they have oysters from as close as Chincoteague Bay, Virginia. East Coast oysters travel from the water to your plate in 24 hours or less.

The Upper Crust Bakery

4 N Pendleton Street (p): 540 687 5666

Hours: Monday – Saturday: 7:30am – 4:00pm, Sunday: Closed

Upper Crust

Upper Crust

Enter The Upper Crust Bakery at your own risk, as the sights and smells are impossible to resist. Pies, bars, buns and cakes are just the beginning. The small, family-owned bakery also does sandwiches, croissants and their most popular item, the Cow Puddle. This crispy and chewy cookie is packed with butterscotch and pecans. Make sure to buy a few, because after one bite, you’ll be hooked!


101 S Madison Street (p): 540 883 3145

Hours: Monday – Thursday: 11:30am – 2:30pm (Lunch) & 5:00pm – 9:00pm (Dinner), Friday – Saturday: 11:30am – 9:30pm, Sunday: 11:30am – 9:00pm

Try Thaiverse on Madison for a unique take on Thai food. Their Masaman Curry is an enticing blend of dried spices, coconut, sweet potato and roasted peanuts. It’s topped with lollipop lamb chops for a dish that is as beautiful as it is delicious.

Popcorn Monkey

101 W Federal Street

Hours: Wednesday – Friday: 11:00am – 4:30pm, Saturday: 10:00am – 4:30pm, Sunday: 11:00am – 4:30pm, Monday –  Tuesday: Closed

Popcorn Monkey

Popcorn Monkey

Retro candy, unique sodas and imaginative popcorn flavors await you at Popcorn Monkey. From green apple to loaded potato, the shop’s popcorn offerings are seemingly endless. Be sure to try the Monkey Mix, a blend of cheddar and caramel, and the Dark Chocolate Sea Salt, their two bestsellers. You can get small, medium or large bags of your favorite flavor, or pack your popcorn in a decorative tin to give as a gift. ML