Nestled in the rolling hills of Virginia’s horse country, Middleburg is a charming town that feels like stepping back in time. This historic gem offers visitors a unique blend of elegant luxury, rich traditions, and countryside beauty that’s hard to find anywhere else.
Whether you’re seeking a relaxing getaway, world-class dining, or exciting outdoor adventures, Middleburg has something special waiting for you.
1. Experience the Horse and Hunt Capital
Middleburg sits at the heart of Virginia’s equestrian world, where horses aren’t just animals but a way of life. The countryside is dotted with magnificent stone-walled farms that look like they belong in a painting.
You can watch thrilling steeplechase races at events like the Middleburg Spring Races, which has been running since the 1900s and is the oldest in the state. Want to get closer to the action?
The Salamander Equestrian Center offers riding lessons for all skill levels, letting you connect with these majestic creatures yourself.
2. Luxurious Resort Getaway at Salamander Middleburg
Picture yourself surrounded by 340 acres of pure relaxation and adventure. Salamander Resort & Spa earned its Forbes Five-Star rating by offering guests an unforgettable experience that blends comfort with excitement.
The spa treatments will melt away your stress, while the fine dining restaurants serve incredible meals made with local ingredients. Feeling adventurous?
Try zip-lining through the trees, take a cooking class from professional chefs, or explore the beautiful grounds on horseback. This resort truly has everything you need for a perfect vacation.
3. Explore the Historic Downtown
Walking through downtown Middleburg feels like entering a storybook village. Over 160 buildings here are listed on the National Register of Historic Places, making this one of the best-preserved small towns in America.
The brick sidewalks and charming architecture remind many visitors of a quaint English countryside town. Every corner reveals another beautiful building with its own story to tell.
The downtown area is compact and walkable, perfect for spending a leisurely afternoon window shopping, grabbing coffee, or simply soaking in the timeless atmosphere.
4. Dine at the Historic Red Fox Inn & Tavern
Established around 1728, the Red Fox Inn & Tavern has welcomed travelers for nearly three centuries. George Washington himself supposedly stayed here, and you can still feel that history in every creaky floorboard and original beam.
The restaurant serves both refined four-course dinners featuring seasonal Virginia ingredients and casual tavern fare in a cozy atmosphere. Imagine enjoying your meal in the same rooms where colonial-era guests once gathered.
The combination of delicious food and authentic historical ambiance makes dining here a truly memorable experience.
5. Indulge in Virginia Wine Country
More than 20 award-winning wineries surround Middleburg, transforming the landscape into a wine lover’s paradise. The local climate creates perfect conditions for growing exceptional grapes, resulting in wines that compete with the best in the country.
Boxwood Winery and Greenhill Vineyards are just two standouts along the Monticello Wine Trail. Each winery offers stunning views of rolling hills and vine-covered slopes.
Spend an afternoon touring different estates, sampling their unique varieties, and learning about the winemaking process from passionate local vintners who pour their hearts into every bottle.
6. Visit the National Sporting Library & Museum
Book lovers and history enthusiasts will find treasure at this unique institution dedicated to country sports. The National Sporting Library & Museum houses the nation’s most comprehensive collection of literature, art, and historical materials related to equestrian activities, fishing, and hunting.
Rare books line the shelves, some dating back centuries, while fine art adorns the walls. The exhibits change regularly, always offering something new to discover.
Even if you’re not particularly interested in these sports, the beautiful presentations and fascinating stories make this museum worth exploring during your visit.
7. Enjoy Boutique and High-End Shopping
Forget generic mall stores, Middleburg’s downtown shopping scene offers something completely different. High-end clothing boutiques, art galleries showcasing local artists, and specialty shops like Crème de la Crème fill the historic buildings.
You’ll find fine jewelry that you won’t see anywhere else, home décor items that add personality to any space, and unique gifts perfect for that hard-to-shop-for person. The shop owners are often there themselves, happy to share stories about their carefully curated collections.
Shopping here feels personal and special, not rushed or overwhelming.
8. Attend World-Class Festivals and Events
Throughout the year, Middleburg hosts events that draw visitors from across the country. The Middleburg Film Festival has become a major stop for Oscar contenders, bringing Hollywood stars and film lovers to this small Virginia town each October.
Christmas in Middleburg transforms the downtown into a winter wonderland, complete with a traditional hunt review where horses and hounds parade through the streets. Other events celebrate the area’s agricultural heritage and equestrian traditions.
These festivals offer entertainment and create a strong sense of community that visitors love experiencing.
9. Discover Local Craft Beverages Beyond Wine
While wine gets much of the attention, Middleburg’s craft beverage scene extends far beyond the vineyard. Lost Barrel Brewing crafts excellent local ales that showcase Virginia ingredients and creative brewing techniques.
Mt. Defiance Cidery & Distillery produces award-winning hard ciders and spirits using traditional methods combined with modern innovation. The tasting rooms provide relaxed atmospheres where you can sample different varieties and chat with the makers.
Many visitors enjoy creating their own beverage tour, hopping between wineries, breweries, and distilleries to experience the full range of local flavors.
10. A Private Escape Close to Washington D.C.
Just one hour from the nation’s capital, Middleburg has served as a countryside retreat for presidents, politicians, and celebrities for generations. Jackie Kennedy famously loved escaping here to ride horses and enjoy the peaceful atmosphere.
Despite being so close to the city, Middleburg feels worlds away from urban stress and noise. The rolling countryside, quiet streets, and slower pace create complete tranquility.
You can easily plan a day trip or weekend getaway without spending hours on the road, making it perfect for busy people who need a quick recharge.
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