The Complete Guide to Visiting Middleburg, Virginia

Dating back to the 18th century, Middleburg is a quintessential small town located in Northern Virginia’s Loudoun County. Known as America’s horse and hunt country capital, the town is home to both the Forbes Five-Star Salamander Middleburg and Red Fox Inn & Tavern, said to be one of the oldest continuously run inns in America.

Middleburg’s brick-lined streets, once frequented by Jackie Kennedy Onassis, are filled with chic boutiques, raffish men’s stores, art galleries, and superb restaurants, while the surrounding countryside is home to horse farms, wineries, breweries, and a craft distillery.

Wine enthusiasts will discover more than a dozen vineyards within 20 miles of the bucolic town, making Middleburg an ideal home base for a Northern Virginia wine tasting weekend. 

THE BEST TIMES TO VISIT MIDDLEBURG

No matter when you visit Middleburg, you’ll discover a pristine small town surrounded by gorgeous countryside landscapes, but the winter holiday season is especially magical. 

The town hosts a tree lighting ceremony, live caroling, and the mile-long Middleburg Hunt & Hounds Review parade. Catch horses, hounds, and riders dressed in full hunting regalia as they march through the decorated streets of Middleburg, ringing in the holiday season in a spectacular and one-of-a-kind way. 

WHERE TO STAY

The Ashby Inn: An Elegant Countryside B&B $$

In the small rural village of Paris, The Ashby Inn & Restaurant is the perfect spot for a romantic getaway. The guest rooms are furnished with 19th-century pieces such as four-poster beds, oriental rugs, and massive hand-painted wardrobes. Several of the rooms have wood-burning fireplaces that create a cozy, welcoming atmosphere during the chilliest nights of the year. 

Salamander Middleburg: Equestrian Extravagance $$$

Equestrian elegance meets modern comfort at the Salamander Middleburg. Each of the spacious rooms and suites features private balconies or terraces, plush bedding, and bathrooms equipped with pedestal tubs and walk-in showers. Sumptuous accommodations are complemented by a bevy of on-site amenities, including a Forbes Five-Star spa, an equestrian center, a zip line course, and on-site hiking trails. 

The Red Fox Inn: Historic Upscale Lodging $$$

Choose from 22 individually decorated rooms, suites, and cottages spread across five meticulously restored buildings at The Red Fox Inn & Tavern. Exuding classic Virginian character, accommodations range from the lively Tavern Suites above the Night Fox Pub to the secluded Stray Fox rooms, the deluxe Carriage House suites with cast-iron soaking tubs, and the private Middleburg Cottage featuring a full kitchen and courtyard access.

Goodstone Inn & Restaurant: A Decadent Dining Getaway $$$

Nestled on a 265-acre estate, Goodstone Inn has six distinct residences with 18 unique luxury rooms, suites, and cottages decorated in English and French country decor. Take a dip in the heated saltwater pool for incredible views of the surrounding countryside and indulge in farm-to-table cuisine at The Conservatory, the inn’s on-site restaurant. 

WHERE TO EAT

King Street Oyster Bar

King Street Oyster Bar provides a casual yet refined setting for seafood enthusiasts and casual diners alike. The menu is centered around fresh, high-quality oysters sourced from the East and West Coasts of the U.S. as well as Canada, but a diverse array of American-style fare and seafood dishes round out the restaurant’s offerings. 

The Conservatory at Goodstone Inn

Experience intimate fine dining at The Conservatory, The Goodstone Inn’s greenhouse-style restaurant. Executive Chef Paul Verica prepares a seasonal Chef’s Table tasting menu that highlights ingredients sourced from the on-site farm and local purveyors. 

Tremolo Bar

This modern wine bar offers an elevated yet approachable dining experience. Helmed by Master Sommelier and James Beard award-nominated chef Jarad Slipp, the menu features internationally inspired small plates such as spicy lamb meatballs and lobster mac and cheese, complemented by a curated selection of over 60 wines available by the glass.

Harrimans Grill at Salamander Resort

Enjoy elevated farm-to-table dining and celebrate the rich culinary heritage of Virginia’s Piedmont region at Harrimans Virginia Piedmont Grill. The menu features seasonal dishes crafted from locally sourced ingredients, including butcher's cuts, fresh seafood, and imaginative desserts. On Sundays, Harrimans hosts a grand family-style brunch featuring a multi-course menu with items like seafood towers, country fried chicken & waffles, and cinnamon-dusted donut holes, often accompanied by live jazz music.

The Red Fox Inn & Tavern

Whether you’re seeking a refined dining experience or a relaxed meal with drinks, The Red Fox Inn & Tavern caters your tastes. The Tavern is an intimate dining area with a seasonal four-course dinner menu featuring local game and seafood dishes, while the Night Fox Pub is a cozy, casual dining space serving pub fare paired with handcrafted cocktails and an impressive selection of wines. 

TOP ATTRACTIONS & LANDMARKS

National Sporting Library and Museum 

The National Sporting Library & Museum explores the heritage of equestrian, angling, and field sports. The museum houses a fine art collection of more than 1,500 objects, such as paintings, sculptures, and decorative arts, as well as a rare book collection with some items dating back to the 16th century.

Aldie Mill Historic Park

Built in the early 1800s, Aldie Mill stands as a unique and well-preserved example of 19th-century milling technology with its twin overshot water wheels. Walk through the four-story brick structure, view the restored equipment, and learn about its role in local commerce and Civil War history through guided tours and live grinding demonstrations.

SHOPPING & SOUVENIRS

Brick & Mortar Mercantile

Located in the heart of downtown Middleburg, Brick & Mortar Mercantile redefines the shopping experience by blending retail with entertainment. Shop a selection of home accents, books, accessories, gifts, and clothing for both men and women. The store often hosts community events, from live music performances and writers' talks to "Paint a Pint" nights, turning shopping into an interactive experience.

Antique Shops in Middleburg

Middleburg's antique shops are situated within the picturesque Middleburg Historic District, established in 1787 and listed on the National Register of Historic Places. The town's antique scene is a blend of traditional craftsmanship and refined taste, making it a must-visit destination for collectors and enthusiasts.

A must-visit antique store is the Middleburg Antique Gallery, which features a diverse selection of 45 dealers offering local, stateside, and European antiques. You’ll find formal English, European, and American furniture, as well as jewelry, lamps, chandeliers, books, oriental rugs, sporting antiques, and fine silver within the massive antique shop. 

Just down the block, the Shaggy Ram is known for showcasing European antiques, furnishings, and accessories for the home.

For those seeking a more curated experience, Another Blue Moon, also located on Washington Street, offers high-quality consignment antiques.

NIGHTLIFE & ENTERTAINMENT

Sip on Craft Cocktails at Nomad

Nomad is a cozy, bourbon-focused bar with a relaxed atmosphere, vintage décor, and a curated jazz playlist. The bar features a selection of top-shelf bourbons, local beers, and a modest menu of bar snacks and small plates. 

Sample Local Ales at Lost Barrel Brewing

Beer enthusiasts should plan a stop at Lost Barrel Brewing to sample some of the 20+ handcrafted brews and hard seltzers. Situated on a historic horse farm, the brewery features a spacious taproom, a cozy porch, and a scenic biergarten with fire pits.

Cheers to Your Vacation at Salamander Resort’s Gold Cup Wine Bar 

Nestled within the luxurious Salamander Middleburg, Gold Cup Wine Bar offers a sophisticated yet relaxed setting for guests to enjoy fine wines, craft cocktails, and gourmet small plates. The bar boasts an extensive selection of local Virginia wines, international varietals, and inventive cocktails.

Toast Like a Colonial at Hunter’s Head Tavern

Though it is about ten minutes outside of Middleburg, Hunter’s Head Tavern feels as if it belongs in the English countryside. The gastropub is located within a restored 18th-century building, and the exposed wooden beams, crackling fireplaces, and rustic decor create a cozy pub vibe. 

Visit Nearby Wineries to Taste Virginia’s World-Class Wines

Part of an area known as D.C.’s Wine Country, Middleburg is surrounded by several award-winning wineries, including Boxwood Winery, Chrysalis Vineyards, 50 West Vineyards, and Cana Vineyards. If you’re a self-proclaimed oenophile, an afternoon spent visiting the wineries should definitely be on your itinerary. 

ANNUAL FESTIVALS

Christmas in Middleburg

When: December 5-7, 2025

Where: Downtown Middleburg

Each year in December, downtown Middleburg is transformed into a festive wonderland. The celebration kicks off on Friday, December 5 with a heartwarming tree lighting ceremony and carol sing-along at the Middleburg Museum. On Saturday, the main event includes a traditional hunt review with mounted riders and hounds, a mile-long Christmas parade with floats, bands, and animals, and the "Spirits of Middleburg" progressive tasting event at local establishments. Sunday ends with a live nativity pageant at Middleburg’s Foxcroft School. 

Middleburg Film Festival

When: October 16-19, 2025

Where: Salamander Middleburg

The Middleburg Film Festival stands out as a top Virginia event for cinephiles, with a curated selection of films in a luxurious setting. Attendees have the unique opportunity to engage with world-renowned filmmakers, actors, and composers through Q&A sessions and panels, fostering a deeper connection with the art of filmmaking. The festival makes a strong commitment to showcasing diverse voices and perspectives, including collaborations with international filmmakers and spotlighting underrepresented narratives.

Middleburg Spring Races

When: April

Where: Glenwood Park

The Middleburg Spring Races, Virginia's oldest steeplechase event, have been a cherished tradition since 1911, drawing thousands to Glenwood Park each April. Experience a unique blend of thrilling equestrian sport and Southern hospitality during the seven races, which are set against the gorgeous backdrop of scenic hunt country. 

Middleburg Oktoberfest

When: September 20, 2025

Where: S. Madison & Federal Streets

Middleburg Oktoberfest turns the town into a festive German-themed village each September. The event features two biergartens offering local beer, wine, and cider, along with traditional German and festival foods. In addition to brews and German foods, Middleburg Oktoberfest has live music, festive games, an art fair with works from local and regional artists, and the popular corgi races.

JUST DOWN THE ROAD…

…Towns to Explore

Purcellville | Purcellville’s beautiful downtown features restored buildings like a former grain mill-turned-restaurant and a 1940s Buick dealership now housing a whiskey distillery. The town boasts a thriving culinary scene, with local favorites such as Tipped Cow Creamery and Magnolias at the Mill, and serves as a gateway to nearby wineries, breweries, and outdoor adventures in the Blue Ridge foothills.

Manassas | Manassas has a balanced mix of rich Civil War history and vibrant modern culture. The nearby Manassas National Battlefield Park provides a poignant glimpse into pivotal moments of American history, and don’t miss exploring the historic district, home to Victorian-era architecture, unique boutiques, and a diverse culinary scene. 

Leesburg | With many examples of well-preserved 18th and 19th-century architecture, Leesburg has a vibrant downtown filled with boutique shops, artisanal coffee shops, and a variety of dining options. Immerse yourself in the town's rich history at sites like Oatlands Historic House, stop into one of the nearby wineries to sample delicious vintages, or bring your bike to ride along the Washington & Old Dominion Railroad Regional Park. 

Winchester | Like Manassas, Winchester has strong Civil War history ties, but you’ll also find musical heritage and small-town charm to round out your visit. Walk the historic Loudoun Street Pedestrian Mall, enjoy local dining and shopping, and delve into the history at sites like Patsy Cline Historic House and Stonewall Jackson's Headquarters Museum. For nearly 100 years, the city has hosted the renowned Shenandoah Apple Blossom Festival in the spring, bringing more than 250,000 visitors to the Shenandoah Valley city. 

…More Outdoor Fun

Sky Meadows State Park | Sky Meadows State Park in Delaplane is an expansive 1,860-acre park filled with rolling pastoral hills, panoramic views of the Blue Ridge Mountains, and 22 miles of hiking trails, including access to the Appalachian Trail. The park also hosts monthly astronomy programs, making it an excellent destination for stargazing enthusiasts. After visiting the park, stop in next door to Ovoka Farms to purchase fresh cuts of farm-raised F1 Wagyu beef. 

Blandy Experimental Farm | Home to the State Arboretum of Virginia, Blandy Experimental Farm is an ideal spot for nature lovers. The serene 712-acre botanical haven offers free admission and is open from dawn to dusk. See more than 8,000 trees and shrubs across 1,000+ species, including the largest boxwood collection in North America and a stunning 300-tree ginkgo grove that turns golden each fall. 

Great Falls Park | A stunning natural escape just 15 miles from Washington, D.C., Great Falls Park is named for the powerful falls of the Potomac River cascading over the jagged rocks into Mather Gorge. There are more than 15 miles of hiking, biking, and horseback riding trails within the park, as well as opportunities for birdwatching, whitewater boating, and learning about the historic Patowmack Canal, one of the nation’s earliest canal systems. 

Shenandoah National Park | One of the most iconic national parks on the east coast, Shenandoah National Park offers over 200,000 acres of natural beauty within the Blue Ridge Mountains. Enter through the northern gateway, located roughly 30 miles from Middleburg, to drive the 105 miles of scenic Skyline Drive. With more than 500 miles of trails, the park caters to all levels of hikers, from the extremely challenging Old Rag Mountain to the family-friendly Dark Hollow Falls Trail. 

Washington & Old Dominion Railroad Regional Park | Bike, walk, or skate along the paved 45-mile trail that runs from Shirlington to Purcellville in Northern Virginia. 

…Noteworthy Attractions

Steven F. Udvar-Hazy Center | The Steven F. Udvar-Hazy Center, part of the Smithsonian National Air and Space Museum, is a must-visit for aviation and space enthusiasts. Located in Chantilly, the expansive facility houses 3,000+ artifacts, including the iconic Space Shuttle Discovery, a Concorde, and the Enola Gay. Admission to the Udvar-Hazy Center is free, but parking is $15 per vehicle. 

Morven Park | Leesburg’s Morven Park has something for everyone—whether you’re looking for history, nature, or equestrian excellence. Stroll through meticulously maintained boxwood gardens, tour the elegant Davis Mansion, and explore over 1,000 acres of scenic trails and woodlands. The park is also home to the renowned Morven Park International Equestrian Center, offering world-class competitions and events for equestrian enthusiasts.

Oatlands Historic House & Gardens | Get a glimpse into early 19th-century plantation life when you tour the restored Greek Revival mansion, walk through meticulously designed gardens, and learn about the lives of those who owned the property as well as those who were enslaved.

…Keep Shopping

Lucketts Store | Lucketts Store is a must-visit destination for vintage enthusiasts and home décor aficionados. Housed in a historic 1879 building in Leesburg, the store offers three floors brimming with unique finds, including antique furniture, architectural salvage, and one-of-a-kind collectibles. 

Whether you’re traveling solo, with friends, or with your family, a Virginia vacation’s got all that you love, all in one place. Use this guide to Middleburg to help you start planning your Virginia vacation today!