Best Restaurants in and Around Middleburg, VA

Nestled in the heart of Virginia’s wine country and known for its stunning horse farms and rolling countryside, Middleburg, VA, is a haven for equestrian enthusiasts and a hidden gem for food lovers. Whether you’re seeking a casual bite after a day of riding or a fine dining experience, the culinary offerings in and around Middleburg are as varied as they are delicious. From fresh oysters to baked goods made with love, this guide will take you through some of the best restaurants in the area that will delight your taste buds.

A must-visit spot for both locals and visitors, Upper Crust Bakery is the epitome of small-town charm and artisanal baking. This quaint bakery is beloved for its freshly baked breads, pastries, and mouthwatering sweets. Whether you’re craving a flaky croissant, a perfectly brewed coffee, or a rustic loaf of sourdough, Upper Crest Bakery delivers with every bite.

Their selection of cookies, pies, and cakes is perfect for any occasion, but don’t leave without trying one of their famous quiches or savory scones, ideal for a light lunch or snack. For those with a sweet tooth, their cinnamon rolls and cow puddle cookies are local favorites. Grab a pastry and enjoy it outside on their patio while taking in the peaceful ambiance of Middleburg.

If seafood is more your style, visiting King Street Oyster Bar is a must. Known for its vibrant and casual atmosphere, this local oyster bar has made a name for itself by serving some of the freshest oysters in the region. Whether you prefer raw, grilled, or fried oysters, King Street Oyster Bar offers a wide variety of options sourced from the best oyster farms along the East Coast.

In addition to oysters, the menu features other seafood favorites like lobster rolls, clam chowder, and crispy calamari. Their raw bar is extensive, and their seafood towers are a show-stopper for those looking to try a bit of everything. Their daily happy hour specials on oysters and select drinks make this spot a popular destination for locals and visitors alike. The relaxed vibe, fresh seafood, and friendly service make King Street Oyster Bar a fantastic place to enjoy a meal with friends or family after a day exploring Middleburg’s countryside.

If you're looking for great food paired with live music, then Red Horse Tavern should be at the top of your list. Located in downtown Middleburg, this cozy pub-style restaurant offers a welcoming atmosphere where you can kick back, enjoy a meal, and listen to live music.

The menu features a range of hearty dishes, from burgers and wings to salads and sandwiches, making it a perfect spot for a casual dinner or a night out with friends.

Known for supporting local musicians, Red Horse hosts live music events several times a week, creating a lively and fun environment. Their outdoor patio is a favorite spot for patrons during the warmer months, where you can enjoy a pint of craft beer and take in the local tunes. Red Horse Tavern is the place to go if you want to enjoy a great meal in a relaxed setting with some of the best live music in town.

A historic landmark in Middleburg, Red Fox Inn & Tavern offers guests a traditional dining experience. Established in 1728, this iconic inn is one of the oldest continually operating taverns in the United States. Red Fox Inn is renowned for its classic American dishes made with locally sourced ingredients, and its charm is only enhanced by the building’s colonial-era architecture and decor.

The menu at Red Fox Inn & Tavern features hearty dishes like braised short ribs, roasted duck, and signature crab cakes. Sunday brunch is particularly popular, offering traditional Southern fare such as biscuits and gravy, chicken and waffles, and seasonal omelets. Paired with a warm, inviting atmosphere, dining at the Red Fox Inn & Tavern is like stepping back in time, making it one of Middleburg's most unique dining experiences.

For those in search of a fine dining experience, Tremolo offers an upscale, sophisticated atmosphere paired with a carefully curated menu that highlights seasonal, locally sourced ingredients. This modern American restaurant serves up a variety of dishes inspired by both classic and contemporary cuisine.

Their menu features everything from perfectly cooked steaks to fresh, creative salads, and decadent desserts. Tremolo’s wine list is extensive, showcasing selections from the surrounding vineyards in Loudoun County, which makes for the perfect pairing with their dishes. Their cozy, refined setting makes Tremolo ideal for a romantic dinner or celebratory meal. Whether you’re indulging in their signature filet mignon or sampling one of their delightful seafood options, Tremolo will leave you with a memorable dining experience.

Located at the luxurious Salamander Resort & Spa, Harrimans Virginia Piedmont Grill provides an upscale farm-to-table dining experience focusing on locally sourced ingredients. The menu is inspired by the rich agricultural heritage of the Piedmont region, offering a range of dishes that highlight the best of Virginia’s farms and fields.

At Harrimans, you can expect expertly prepared steaks, fresh seafood, and creative vegetarian options. Their extensive wine list includes both local and international selections, ensuring the perfect pairing for every meal. The restaurant's elegant, rustic-chic decor, combined with its stunning views of the surrounding countryside, makes Harrimans a fantastic choice for special occasions or a romantic night out.

If you're a wine lover, The Wine Kitchen in nearby Leesburg is worth the short drive from Middleburg. This farm-to-table bistro offers an impressive selection of wines by the glass and a seasonal menu that changes frequently to reflect the freshest local ingredients.

The Wine Kitchen’s menu features a variety of small plates and entrees, including house-made charcuterie, fresh salads, and perfectly cooked meats. Their carefully curated wine list pairs beautifully with the dishes, making this spot a favorite among both foodies and wine enthusiasts.

Middleburg and its surrounding areas offer an incredible range of dining options, from casual eateries to fine dining establishments. Whether indulging in oysters at King Street Oyster Bar, enjoying live music at Red Horse Tavern, or savoring a gourmet meal at Tremolo, there's something for every palate. When exploring the Middleburg countryside, be sure to check out these local favorites and make your dining experience just as memorable as the scenic beauty of the area.

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