Picture yourself cruising along winding country roads, passing white-fenced horse farms, historic stone mansions, and rolling green hills with the Blue Ridge Mountains rising in the distance.
That’s exactly what you’ll find on a Virginia Hunt Country road trip, where charming small towns, centuries-old landmarks, beautiful vineyards, and some seriously gorgeous countryside are waiting around every corner.
This part of Northern Virginia is famous for its horse racing traditions, grand estates, and historic villages, but there’s so much more to discover beyond the fancy farms and beautiful scenery.
Ready to hit the road? Here’s how to explore the best of Virginia Hunt Country, one amazing stop at a time!
1. Bear’s Den Scenic Lookout
Bear’s Den Scenic Lookout is one of the best places to catch a stunning sunset in Virginia Hunt Country, located along the Appalachian Trail near Bluemont, just off Route 7 on the Blue Ridge Mountains.
Perched about 1,350 feet above sea level, this rocky overlook offers sweeping views of the Shenandoah Valley, with rolling mountains, thick forests, and colorful fall foliage stretching into the distance.
You can reach the lookout with a short, roughly 0.4-mile round-trip walk from the Bear’s Den day-use parking area.
The lookout is also part of the famous 2,190-plus-mile Appalachian Trail, and nearby Bear’s Den Trail Center occupies a historic stone mansion built in the 1930s.
2. Oatlands Historic House & Gardens
After soaking up the mountain views at Bear’s Den, head to Oatlands Historic House & Gardens, a beautiful 418-acre estate near Leesburg, where you can explore a grand 19th-century mansion, formal gardens, and centuries of Virginia history.
Built in 1804 by George Carter, the stately Federal-style mansion features elegant rooms, original architectural details, and guided tours that reveal stories about the Carter family and the enslaved people who lived and worked on the property.
Outside, you can wander through a 4.5-acre English-style terraced garden filled with flower beds, winding paths, towering boxwoods, and colorful seasonal blooms, including gorgeous peonies in spring.
Oatlands is also a National Historic Landmark, and its grounds offer a fascinating look at the plantation’s past, making it one of Loudoun County’s most interesting historic stops.
3. Aldie Mill Historic Park
Continue your Virginia Hunt Country road trip to Aldie Mill Historic Park, located along Little River in the tiny village of Aldie, where a beautifully preserved 19th-century gristmill takes you back to Virginia’s early farming days.
Built between 1807 and 1809, this four-story brick mill once used waterpower to grind local farmers’ wheat and corn into flour and meal, making it an important part of the region’s agricultural economy.
During select demonstrations, you can watch the mill’s massive waterwheels and historic grinding machinery in action, while guided tours reveal how grain traveled through the building using wooden gears, belts, and elevators.
The park also features a historic miller’s house, scenic creek views, and connections to the Civil War-era village.
4. Greenhill Vineyards, Middleburg
After exploring the old waterwheels at Aldie Mill, head about 5 minutes to Greenhill Vineyards, a beautiful 128-acre winery just outside downtown Middleburg, where you can sip a glass of locally made wine.
Located along scenic Route 50, this boutique winery is known for its award-winning wines, including Cabernet Franc, Chardonnay, and Blanc de Blancs sparkling wine, all produced using grapes grown in Virginia.
You can enjoy a guided wine tasting, grab a bottle to share, or relax on the outdoor patio overlooking rows of grapevines, rolling hills, and the surrounding horse farms that make Middleburg famous.
The property also features a peaceful pond, a historic stone manor house, and beautiful countryside views, making it a fantastic afternoon stop before exploring Middleburg’s charming shops and restaurants.
5. Middleburg
After sipping wine at Greenhill Vineyards, head into downtown Middleburg, a charming small town founded in 1787 that’s known as the “Nation’s Horse and Hunt Capital” thanks to its famous foxhunting traditions, horse farms, and equestrian events.
Stroll along Washington Street, where historic brick buildings house boutiques, antique shops, art galleries, and local favorites like the Middleburg Common Grounds coffee shop and the Red Fox Inn & Tavern, which dates back to 1728.
For a closer look at the town’s horse-loving roots, visit the National Sporting Library & Museum, home to paintings, sculptures, books, and exhibits celebrating horses, foxhunting, and country sports.
If you’re visiting in December, don’t miss Christmas in Middleburg, when horses, hounds, and riders parade through downtown in festive holiday style.
6. The Plains
From Middleburg, continue about 15 minutes to The Plains, a tiny Fauquier County town where historic buildings, horse farms, and a handful of excellent restaurants make for a fun stop on your road trip.
Start on Main Street, where you’ll find charming 19th-century storefronts, independent shops, and The Rail Stop Restaurant, a local favorite serving contemporary American cuisine.
For something special, visit The Ashby Inn & Restaurant, a historic inn dating back to 1829 that’s known for its seasonal dishes and beautiful countryside setting.
Just outside town, Great Meadow is a 374-acre equestrian event venue famous for hosting the Virginia Gold Cup steeplechase races, where horses race over fences each spring.
7. Sky Meadows State Park
Next, head to Sky Meadows State Park near Delaplane, where more than 1,800 acres of open meadows, wooded hills, and Blue Ridge Mountain views offer some of the prettiest hiking in Virginia Hunt Country.
The park features over 20 miles of hiking trails, including the popular 0.6-mile Piedmont Overlook Trail, which climbs through grassy fields to a scenic viewpoint overlooking the rolling countryside and distant mountains.
You can also explore the Mount Bleak House, a preserved historic farmhouse built in the early 1840s, where exhibits share stories about the families and farmers who once worked this land.
For extra adventure, hike a section of the Appalachian Trail, enjoy a picnic beneath the trees, or visit in fall when the meadows turn golden.
8. Upperville
Wrap up your Virginia Hunt Country road trip in Upperville, a tiny village along Route 50 in Fauquier County, famous for its historic stone buildings, white-fenced horse farms, and deep equestrian traditions.
Founded in 1797, Upperville is home to the Upperville Colt & Horse Show, America’s oldest horse show, which began in 1853 and still attracts top riders for exciting jumping competitions every June.
Take a stroll through the village to admire its 19th-century homes, visit the historic Trinity Episcopal Church, or stop by Hunter’s Head Tavern, a cozy restaurant housed in a building dating back to the 1700s.
Just outside town, you’ll find Oak Spring Garden Foundation, the former estate of philanthropist Bunny Mellon, whose famous gardens are accessible through limited ticketed visits and special programs.
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