From Middleburg to Hamilton: A Weekend in Loudoun County

Photo Courtesy of Visit Loudoun.



Experience the charm, hospitality and picturesque views of Loudoun County’s small towns and villages on the perfect weekend getaway. From Middleburg to Hamilton, tour museum exhibits, explore local markets, sample regional wines and escape into the rolling hills of Virginia’s pastoral countryside.

Wherever your adventures may lead, expect new experiences on and off the beaten path in Loudoun County. 

Day 1: Middleburg to Round Hill 


In the charming horse country town of Middleburg, fuel up for the day at The Upper Crust, a no-frills breakfast spot beloved by locals. Tucked away on North Pendleton Street, it’s the perfect spot to indulge in a cup of coffee and a delicious fresh-baked ham and cheese croissant. Be sure to order a to-go box of lemon bars, a berry pie or the cow puddle cookies, a longtime favorite at the establishment – they’re buttery, chewy and perfect for the road.

The National Sporting Library & Museum in Middleburg, Virginia. Photo Courtesy of Visit Loudoun.

Once you’ve gotten your fill of savory and sweet, make your way to the National Sporting Library & Museum — a brisk walk or a short car ride away. Open Thursdays through Sundays, this ode to the area’s horsemanship, field sports and fox-hunting heritage is home to a six-acre campus brimming with art collections and rare books, from colorful horse paintings to equine statues forged from bronze.

After you’ve browsed the museum, why not indulge in some morning retail therapy? Downtown Middleburg’s local shops offer an eclectic variety of goods. For example, at Highcliffe Clothiers, the staff can help you dress the part for your Loudoun County explorations, whether you’re in the market for buttery leather riding boots, a tailored dinner jacket or a jaunty bowtie. Don’t miss out on cool souvenirs at The Fun Shop. Choose from an assortment of items, from Middleburg Christmas ornaments to kitchenware, gardening tools, and fox and horse artwork. And don’t forget The Christmas Sleigh for a range of German nutcrackers, handcrafted ornaments, beer steins and traditional German stollen.

No matter the time of year, you’re likely to find special events on the town calendar, including Christmas in Middleburg, the Middleburg Summer Sidewalk Sale in August and April’s Middleburg Spring Races, which gives you a chance to experience the area’s rich horse racing culture.  


Once you’ve explored all Middleburg has to offer, drive a few miles northwest to Bluemont, an area dotted with breweries and vineyards set against the backdrop of the exquisite Blue Ridge Mountains. Feast in the sunlight on the Bluemont Vineyard terrace, reserve a table indoors, and order up flatbreads, or enjoy a luxury picnic with a delicious assortment of charcuterie, cheeses and pastries. Wine aficionados and novices alike are sure to find a blend that meets their tastes, such as the Farm Table white or red. Sip a glass while taking in the sweeping vineyard scenery.

After lunch, take a short hike along a heavily treed section of the Appalachian Trail to reach Bear’s Den Overlook for a quick family photo op on a rocky outcropping with lush valley views below. Then make your way back down the trail and enjoy a refreshing after-hike beer in the nearby Bear Chase Brewery taproom. 


Call ahead to make reservations at the Airwell Bed and Breakfast, a cozy getaway near the Blue Ridge Mountains. Or go for luxury accommodations at The Manor at Airmont. This five-bedroom 1830s home includes wide porches, sprawling grounds and iron scrollwork banisters. 

The Manor at Airmont in Round Hill, Virginia. Photo Courtesy of Visit Loudoun.

Once you’ve checked in, head to Round Hill’s Hill High Marketplace, a former orchard-packing space turned tourism experience. You can pick up a flaky-crust pie filled with sweet Shenandoah apple filling at the appropriately named Mom’s Apple Pie, bring back a souvenir bottle from Bogati Winery, or pick up an art print or original piece of work at Round Hill Arts Center or Gateway Gallery

Cap off your day at More Better Restaurant and Beer Hall to feast on Bavarian dishes such as jagerschnitzel and currywurst while sipping a grapefruit Hefeweizen or Hofbrau Original. 

Day 2: Hillsboro to Hamilton 


Kick off the morning with a scenic drive north toward the gently curving roads of rural Hillsboro. Snap photos of the stunning green hills dotted with historic stone buildings, or stop for a tasting at a brewery or winery along the way.

The Stoneybrook Farm & Market in Hillsboro, Virginia. Photo Courtesy of Visit Loudoun.

Grab breakfast at Stoneybrook Farm & Market, situated on 45 acres of picturesque farmland. Order an Old St. Joe’s master blend coffee or chai latte to complement your scone or sweet roll. Just be sure to check the calendar before you go; the market is closed on Saturdays and for Yom Kippur and Sukkot. And don’t pass up the opportunity to purchase a crusty loaf of sourdough to take home. 

Next, head to Purcellville, a bustling rural town with plenty of things to see, sip and savor. Browse the aisles of Nostalgia Boutique for vintage clothing and antique furniture, or find a treasure from Graffiti + Silk, an artsy-modern thrift store benefiting Mobile Hope’s mission to fight homelessness and food insecurity. Then pop into M. Franklin Studio & Boutique, a women’s clothing store offering everything you need — from jewelry and makeup to shoes and clothing — to create an upscale look. 


For mouthwatering barbecue, Monks BBQ is the place to be. Order a lunch plate of tender brisket, falling-off-the-bone ribs, and a side of cornbread custard or bacon on a stick. If you’re feeling extra hungry, try the Boss Hog platter. It includes all the meat Monks has to offer, with Texas toast on the side. Wash down your BBQ with a local brew, like pilsner or cider. 

After lunch, why not burn off the barbecue with a stroll on the nearby Chapman DeMary Trail? The path offers scenic views of the South Fork Catoctin Creek. Next, pay a visit to Catoctin Creek Distilling Company and experience a tasting of Virginia’s most awarded Roundstone Rye whisky, along with a tour to learn more about its production. If you’d prefer something more exhilarating, Elysium Axe Throwing will give you a rush as you order a draft beer and hawk an ax at a target. 


Depending on the time of year, spend the late afternoon at Wegmeyer Farms in Hamilton to pick plump raspberries, blackberries, strawberries, and pumpkins or sunflowers. Then, pop into the tasting room at The Barns at Hamilton Station Vineyards, a converted dairy farm offering a variety of regional blends, including a rich Meritage and citrusy Viognier. 

The Barns at Hamilton Station Vineyards in Hamilton, Virginia. Photo Courtesy of Visit Loudoun.

End your evening by ordering a large platter of fried fish, briny Chesapeake Bay, Chincoteague oysters, or crab at Lowry’s Crab Shack.

More of Loudoun County 

One weekend isn’t enough to scratch the surface of all Loudoun offers. So if you’re itching to spend more time in the area, be sure to check out more of Loudoun County’s villages and sites, including a 1700s post office in Waterford and local art installments in Leesburg.  

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