DESTINATIONS

The Guide to Living in Upperville, Virginia

In the heart of Virginia Hunt Country, an iconic equestrian enclave on the foothills of the Blue Ridge Mountains

UPPERVILLE, VIRGINIA

The History of Upperville, Virginia

Located in the heart of Virginia Hunt Country, the historic town of Upperville, Virginia offers the ideals of small town charm along the foothills of the Blue Ridge Mountains.

Established in 1797 by Josephus Carr along the Alexandria-Winchester Turnpike, Upperville, Virginia today is regarded as one of America’s most revered equestrian communities.

Despite its status as one of Virginia’s smallest town, Upperville, Virginia is the birthplace to many iconic Mid-Atlantic and Virginia Hunt Country traditions.

The Upperville Colt & Horse Show, established in 1853 by Richard Henry Dulany, represents the oldest continuously running horse show in the United States.

A designated landmark on the National Register of Historic places, Upperville, Virginia is also home to many of America’s most iconic country homes and estates, including Sandy Lerner’s Ayrshire Farm and Paul and Bunny’s Mellon’s Oak Spring Garden Foundation estate as well as a variety of charming 19th-century style brick, wood, and log homes along the upper-end of the town’s main thoroughfare.

Among its most notable architectural structures, Trinity Episcopal Church stands as one of the most significant in Upperville, Virginia. Designed by H. Page Cross in the French medieval parish style, it was donated by philanthropist Paul Mellon in the 1950s.

And for lovers of the outdoors and adventure, Sky Meadows State Park offers access to the Appalachian Trail and stunning vistas of the Blue Ridge Mountains across over 1,000 acres of protected park land.

THE HOMES COLLECTION

The Homes of Virginia Hunt Country

Discover the most iconic homes of Virginia Hunt Country

UPPERVILLE, VIRGINIA

“I’ve always known there was a town just right for me; I’ll settle down and be uplifted all day long— fair Upperville, accept my song.”

— John Updike

  UPPERVILLE, VIRGINIA

Photo Gallery

Browse high-resolution photos of Upperville, Virignia courtesy of Hugh Kenny

 UPPERVILLE, VIRGINIA

Frequently Asked Questions

Explore common questions about life in Upperville, Virginia, including the best neighborhoods, restaurants, and more

HOW MUCH DOES IT COST TO BUY A HOME IN UPPERVILLE, VIRGINIA?

The median sale price for a single family home in Upperville, Virginia is $492,950, which is about 40% higher than the national average of $308,980. Ready to buy the home of your dreams? Browse homes for sale in Upperville, Virginia presented by Sotheby’s International Realty.

HOW MANY PEOPLE LIVE IN UPPERVILLE, VIRGINIA?

According to the 2020 Census data, Upperville, Virginia has a population of only 178 people, including a median age of 61 and a median household income of $73,164.

WHAT IS THE PROPERTY TAX RATE FOR UPPERVILLE, VIRGINIA?

Property taxes for Upperville, Virginia are levied by Fauquier County at a rate of $0.943 per every $100 of assessed value. Property taxes are comprised of a base rate of $0.759, an additional $0.180 fire and rescue levy, and a $0.004 allocated towards the county wide conservation easement fund.

WHAT ARE THE BEST RESTAURANTS IN UPPERVILLE, VIRGINIA.

Despite being one of the smallest towns in the Mid-Atlantic, Upperville, Virginia boasts two amazing restaurants. The iconic Hunter’s Head Tavern offers fresh English country fare, including Shepherd’s Pie, Fish and Chips, and Guinness on draft. Just down the road, Bluewater Kitchen offers delicious scratch-made American fare and a charming market offering prepared foods and sundry items.

WHAT IS THE SCHOOL DISTRICT FOR UPPERVILLE, VIRGINIA?

Residents of Upperville, Virginia attend Fauquier County Public Schools.

WHEN IS THE UPPERVILLE COLT & HORSE SHOW?

Established in 1853, the Upperville Colt & Horse Show is an annual equestrian event that takes place at the Grafton and Salem Show Grounds in Upperville, Virginia. The 172nd Upperville Colt & Horse Show begins on June 2, 2025 and concludes on June 8, 2025.

HOW FAR IS UPPERVILLE, VIRGINIA FROM WASHINGTON, D.C.?

Upperville, Virginia is approximately 60 miles from downtown Washington, D.C. The most common way to get to Washington, D.C. from Upperville, Virginia is via car.

THE RAPPAHANNOCK RIVER COMPANY

Find a Trusted Design Professional in Upperville, Virginia

Explore the very best Residential Architects, Custom Home Builders, Interior Designers, and Landscape Architects near Upperville, Virginia

The Sageview Estate of Upperville, Virginia. Image courtesy of Studio Trejo.

 MIDDLEBURG, VIRGINIA

Clites Architects

Clites Architects is a Residential Architecture Firm in MIddleburg, Virginia

Learn More »

Westwood of Vienna, Virginia. Image courtesy of Erik Kvalsvik.

MIDDLEBURG, VIRGINIA

Neumann Lewis Buchanan

Nuemann Lewis Buchanan is a Residential Architecture Firm in Middleburg, Virginia

Learn More »

Saddleback Farm of Afton, Virginia. Image courtesy of Greg Goodson.

MIDDLEBURG, VIRGINIA

Jacobsen Architecture

Jacobsen Architecture is a Residential Architecture Firm in Middleburg, Virginia

Learn More »

THE RAPPAHANNOCK RIVER COMPANY

Create Your Next Home in Upperville, Virginia

With our premium concierge service, it’s never been easier to create the home of your dreams