After a long winter in lockdown, I was desperate for a getaway that would feel transporting, even though I didn’t want to drive very far. So I headed south from bustling Washington, D.C., breaking free of the traffic on the Beltway and driving past the Virginia suburbs just outside the city. Just an hour’s drive away, I found myself surrounded by bucolic bliss in Middleburg, Virginia.
Middleburg is the heart of Loudoun County, the fifth-largest wine-producing region in the country, nestled in the foothills of the Blue Ridge Mountains. Not only are there 30 wineries nearby, making Middleburg the perfect perch for wine lovers, but the town of just 539 full-time residents boasts 160 buildings on the National Register of Historic Places, so it’s a draw for history buffs as well. And since it’s the horse and hunt capital of the United States, equestrians will find a lot to love here, too. (The town was a favorite of horsewoman Jackie Kennedy Onassis, who kept a home here.)
The whole area is so lush and green that it reminded me of the Irish countryside, but with the touches of Southern charm and friendliness that are the hallmarks of Charleston and Savannah. Here’s what I discovered on my trip.
I was a guest of the Salamander Resort and Spa, but all opinions and recommendations are my own.
Things To Do In Middleburg
Middleburg is the quintessential small town, with a walkable main thoroughfare offering myriad opportunities for shopping, eating, and exploring. There are also plenty of opportunities to enjoy the vast outdoor areas that surround the town.
Stroll And Shop On Washington Street
Although the central thoroughfare in Middleburg is called Washington Street, in my mind I can’t help but call it “Main Street,” since it has such a classic small-town layout and feel. Lining both sides of the street for about half a mile are buildings dating to the 18th century that contain shops, galleries, and restaurants. Due to the cozy layout, it’s easy to just wander and explore until something catches your eye, but don’t miss The Fun Shop, a general store-meets-department store-meets maze. Its two floors feature everything from housewares and Hunt Country gifts to children’s toys and gourmet goodies. The first person who told me about the shop gave a solid piece of advice: If you can’t find it there, you probably didn’t need it in the first place.
Enjoy The Wine, Beer, And Cider
Winemaking has been a tradition here in the Piedmont region of Virginia since colonial times. The wineries have recently been joined by both breweries and cideries, so there are plenty of opportunities to sip, relax, and enjoy the views, no matter what your drink preference is.
Boxwood Winery combines new wine techniques with a historic landmark farm, all nestled on 26.5 gorgeous acres planted with traditional Bordeaux varietals. Mount Defiance Cider Barn is located right on Washington Street, which makes it easy to indulge and then walk back to your accommodations. For beer lovers, Lost Barrel Brewing and Old Ox Brewery are nearby, too. And to safely extend your tour to include multiple wineries, check out Expedition Vintage Tours, which will bring you to local wineries or breweries in a classic Land Rover.
Visit The National Sporting Library & Museum
Whether you’re a true horse fanatic or just want to know more about the tradition of riding and hunting, you’ll find something of interest at the National Sporting Library & Museum. The museum’s mission is to preserve the history of all field sports, meaning fishing, foxhunting, polo, and horse racing. This one-of-a-kind spot comprises two buildings. You’ll see oil paintings and a stunning silver tabletop riding carriage and horses that once belonged to Alfred G. Vanderbilt. Although there are some angling paintings, mostly what you’ll see are exquisite portraits of horses and hounds in different settings — all of which are displayed in the perfectly preserved Duffy House, circa 1820. The more modern library next door houses rare books and is open by appointment only. (If you visit the library, ask to see the hand-painted fore-edge books, with intricate scenes painstakingly painted on their page edges.)
Saddle Up For A Horseback Ride
Inspired by all of the equestrian history in Middleburg? You can saddle up at The Salamander Resort’s stables. In addition to trail rides on 25 private acres, the resort offers lessons in dressage, or different seatings for hunting or showing. Even if you don’t feel up to riding (which I didn’t when I was in town), you can still spend time with the stunning steeds, since the stables are open to visitors every day from 9 a.m. to 3 p.m.
Try A New Outdoor Activity
Even if you don’t ride a horse when you’re in Middleburg, you’ll be able to enjoy other adrenaline-pumping activities. Empower Adventures offers treetop zip-lining and rappelling, for instance. Since I like to keep my feet firmly on the ground, I skipped those, but I broke out of my comfort zone to try axe throwing and archery. Although I wasn’t sure about those sharp-sounding activities at first, with expert instruction in a very large, outdoor, remote area, I was surprised how many times I was able to hit the target. A bonus? It was a hit with everyone in my multigenerational travel group. Oh, and now I’m ready for the zombie apocalypse!
Welcome Spring At The Races
Many locals consider the Middleburg Spring Races the official start of spring in Virginia. The century-old steeplechase highlights the region’s best equestrians, and even if you don’t know a lot about horse racing, the gorgeous green-grass track, high-jumping horses, and high-end tailgating are still very entertaining as well as a great introduction to the nation’s horse and hunt capital.
For a small town, Middleburg offers some big tastes of Virginia farm-to-table and sea-to-fork cuisine, not to mention Southern favorites that’ll make you feel like you’ve landed much farther than you’ve actually traveled.
King Street Oyster Bar
Although Middleburg isn’t on the water, Virginia’s coastline isn’t far away, and King Street Oyster Bar capitalizes on this accessibility by serving some of the area’s freshest and most flavorful seafood. As the name suggests, oysters are a specialty here, and you can choose from 10+ varieties on any given day, including a number of options from both Virginia and Maryland’s Eastern Shore. Other menu highlights include Maryland crab cakes, North Carolina trout, and fish and chips, plus chicken, salad, and sandwich options, too. There’s a large section for outdoor dining. Don’t miss the $1 oyster happy hour every evening from 3 p.m. to 6:30 p.m.
Red Bar Sushi
You may not immediately think “sushi” when you’re in horse country, but Red Bar Sushi on Washington Street is worth a stop. Not only does this Japanese restaurant make all of its own sauces and dressings for its salads, sushi, and noodle dishes (the carrot ginger salad topper is to die for), but it uses some of the freshest local seafood that I’ve ever had. One highlight: the California roll, which includes fresh Maryland crab. It’s a revelation.
Harrimans Virginia Piedmont Grill
If, after a long pandemic year, you’re ready to dress up a bit, Harrimans Virginia Piedmont Grill is the place to go for a special dinner or just to celebrate getting out of the house. The elegant dining room at The Salamander Resort has horse-country details and fabulous wide windows that offer great views of the lush landscape outside. The menu highlights regional, seasonal ingredients — including, on my recent visit, a salad with shaved asparagus and English peas that tasted like spring in a bowl — and steakhouse and seafood favorites, including grilled wagyu beef. Another way to enjoy the gorgeous dining room: Stop in for breakfast or brunch. If you do, don’t miss the billowing biscuits, fried chicken, and decadent cheese grits.
If you’re looking for the insider pick for Middleburg, this unassuming wine store is where to go. I had locals tip me off on this Main Street shop before I arrived in town, and I even heard some women whispering about it while they were sipping cocktails on the porch at The Salamander. The draw? Knead offers hidden-gem wines, half of which are just $20, and gourmet pizzas created by Jarad Slipp, a master sommelier with degrees from the Culinary Institute of America and the ICIF in Italy.
While Middleburg is a small town with a big resort, The Salamander, there are a variety of other places where you can spend the night. You’ll find an array of cottages and farmhouses on platforms such as Airbnb and Vrbo, and there are a number of small, quaint bed and breakfasts in the surrounding area. The Red Fox Inn & Tavern has been welcoming visitors in some form since 1728.
The Salamander Resort And Spa
Although I’ve lived in and explored around Washington, D.C., I had no idea there was a resort as luxe and large as The Salamander until recently, when I was looking for a pandemic-friendly getaway. Middleburg is just off the beaten path enough that this sprawling property with stables, pools, a destination spa, and gourmet restaurants has managed to stay under the radar. As I headed up the meandering drive, it truly felt like I had traveled much farther than an hour from D.C.
The plush rooms all have balconies overlooking the sprawling grounds. The gas fireplace and freestanding deep soaking tub in the marble bathroom made me feel like I was on vacation before I even explored the resort. There’s also a large fireplace in the high-ceilinged library lounge, the perfect spot to cozy up with an after-dinner drink.
Since I visited in the early spring, I wasn’t able to use the outdoor pool, but I was able to take a dip in an indoor one. There’s a destination spa here, too, with outdoor heated soaking pools. Hiking and biking are great ways to explore the property and the surrounding area. My family rented bikes and peddled past the tennis and basketball courts to the palatial stables to meet local celebrity pony Cupcake. The pony makes appearances at weekend-evening happy hours; we missed her star turn, but we did get to enjoy the fire pits and s’more-making under the stars, an evening activity I highly recommend for the full vacation experience.
Pro Tip: For a Currier and Ives experience, visit Middleburg at Christmas, when the annual Hunt and Hound Review fills Washington Street with a menagerie of mounted foxhunt riders and handsome hunting dogs.