Historic Upperville is an equestrian escape in Virginia’s Hunt Country
In the heart of Virginia Hunt Country, Upperville is a historic village known for its equestrian heritage and time-honored country estates. Residents embrace the Hunt Country lifestyle year-round, particularly at the Upperville Colt & Horse Show, which was founded in 1853 and is the nation’s oldest horse show. “During the Upperville horse show, there are quite a few people here because it's a big destination. People come from all over the country,” says Cindy Polk, a local real estate agent with Compass who specializes in selling country properties in the area. “But in general, just in other times of the year, it's the horse culture and the history that draws visitors… It’s a quaint blink of a town with some beautiful old homes.” While Upperville is known as the village that’s “a mile long and an inch wide,” its cultural legacy stretches far beyond its borders toward the regional hub of Middleburg , less than 10 miles east.
Old homes, farmhouses and estate properties with horse facilities
The Upperville Historic District preserves the village’s original homes along U.S. Route 50. These properties showcase Federal, Georgian, Greek Revival, Colonial Revival and Craftsman styles, with a few cottages in the mix. Weathered stone walls and manicured hedges enhance the country atmosphere. Houses of worship include the Gothic Revival-style Upperville Baptist Church and the French-inspired Trinity Episcopal Church, a gift from philanthropists and former residents Paul and Bunny Mellon. “It's the centerpiece of the village, a really lovely, impressive architectural stone building with a courtyard. It hosts the annual Hunt Country Stable Tour in May, where folks take a driving tour through some exceptional country properties,” Polk says.
Farther from the highway, country estates and farmhouses stretch across rolling hills. “The side roads going north and south are meandering, bucolic country roads,” Polk says. Some properties span more than 100 acres, and those with barns, paddocks and horse stalls attract equestrian enthusiasts. Prices vary widely due to Upperville’s unique mix of homes. The median sale price is $1.3 million, and on average, properties sell in less than a month. Upperville's CAP Index Crime Score is 1 out of 10, well below the national average of 4.
Riders of all skill levels attend the Upperville Colt and Horse Show
The Upperville Colt and Horse Show is held each June at the Grafton and Salem Farms Showground, just outside of Upperville. The week-long event features world-class jumper and hunter competitions, including the Upperville Jumper Classic CSI4* and the USHJA International Hunter Derby, alongside amateur- and junior-level competitions. Spectators can also enjoy tailgating, an antique car show, an extravagant hat competition and other equestrian-themed activities throughout the week.
From foxhunting culture to hiking trails in Sky Meadows State Park
Horseback riding and foxhunting are popular pastimes. Equestrian facilities offer boarding and training, and the Piedmont Fox Hounds is the country’s oldest organized fox hunt. The estate of Paul and Bunny Mellon is now run by the Oak Spring Garden Foundation, a nonprofit organization that preserves Mrs. Mellon’s horticultural collections. The estate is open during Virginia Historic Garden Week and hosts workshops year-round. Upperville Park has a ballfield and playground, while Goose Creek Historic Park draws Civil War buffs to the site of the Battle of Upperville.
Outdoor enthusiasts can head 5 miles west to Sky Meadows State Park. The 1,862-acre green space is known for its hiking trails and access to the Appalachian National Scenic Trail. Conservation easements around the state park and Upperville help preserve the region’s rural character.
Small-town businesses close to historic downtown Middleburg
A few Hunt Country-inspired businesses serve the community. CS Arms is an antique store showcasing military memorabilia, while Trinity Thrift & Boutique sells vintage goods in line with the region’s equestrian aesthetic. Residents can pick up outdoor essentials at The Farm Store by EverGRO. A restored 18th-century home houses the Hunter’s Head Tavern, a British-style gastropub serving farm-to-table comfort foods made with meats from Ayrshire Farm. Downtown Middleburg has more shops and restaurants, including upscale boutiques and fine-dining establishments. Safeway, just over 8 miles away, is the closest grocery store. Wineries and breweries dot the surrounding countryside.
Education at Fauquier County schools and top-rated private schools
The Fauquier County Public Schools district earns a B from Niche and has an average student-to-teacher ratio of 13-to-1. Claude Thompson Elementary School receives a C-plus, while Marshall Middle School scores a B-minus. Fauquier High School earns a B and has a robust career and technical education department with courses in agriculture education, business and marketing, STEM and technology education, and more. Private school options include The Hill School, a co-educational day school serving prekindergarten through eighth grade with an A-plus from Niche. For girls in ninth through 12th grade, Foxcroft School ranks as the best private high school in Loudoun County.
U.S. Route 50 provides access to D.C. and nearby highways
A lack of public transportation makes Upperville a heavily car-dependent area. U.S. Route 50, a commuter route between Northern Virginia and Washington , connects residents to Interstate 66, and the drive to the capital is about 62 miles. Washington Dulles International Airport is roughly 30 miles away. “You're within an hour of Dulles International Airport, which I think is pretty critical, and you're within an hour and 20 minutes or so from D.C.,” Polk says. StoneSprings Hospital Center is approximately 20 miles from Upperville.
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Written By
Sally Stimpson
