Virginia's Quaint Village Near Washington, DC Has History, Architecture, And A Cozy Tavern

About 60 miles west of America's capital, the national monuments and government offices give way to Route 50, bordered by rolling fields, bucolic farms, family-owned vineyards, and historic villages that lie in the shadow of the Blue Ridge Mountains. For ages, Washingtonians have escaped to these scenic Virginia landscapes for a taste of countryside living. Famous figures such as President John F. Kennedy and Jackie Kennedy, Elizabeth Taylor and her former husband Virginia Senator John Warner, and banking heir Paul Mellon and his wife Rachel "Bunny" Mellon owned estates in the area. While most of the action centers around Middleburg, Virginia's horse-and-hunt hamlet with vintage charm, vineyard sips, and boutiques, in-the-know travelers venture about another 8 miles down Route 50. There, centuries-old stone walls enclose sweeping fields and farms in the petite community of Upperville.

Established in the mid-to-late 1700s, Upperville is largely residential today, with grand farms and estates tucked behind long driveways. The Upperville Historic District spans a number of preserved buildings built between the 18th and 20th centuries. This includes the Upperville Library, the Trinity Episcopal Church, and the Old Carr House, which was transformed into the Hunter's Head Tavern, a cozy spot for hearty meals. Other Upperville landmarks include Slater Run Vineyards for wine tastings and Bunny Mellon's Oak Spring Garden, only open to the public a few times each year. Visitors also descend upon Upperville each June for the Upperville Colt & Horse Show, which has been held since 1853 and is the country's oldest horse show.

Find this town a roughly 70-minute drive from Washington, D.C. and a 50-minute drive from Dulles International Airport, the nearest major airport. The best times to visit Upperville and neighboring Middleburg are spring and early summer for colorful blooms and fall for cool weather and brilliant foliage.

Though much of Upperville's idyllic landscape is privately owned, a scenic drive down Route 50 will introduce visitors to local vistas and historic buildings. Along the way, you will bypass the towering steeple of Trinity Episcopal Church, a French Norman-inspired structure on a 35-acre campus. Though the parish dates to the 1800s, the church itself was rebuilt in its current style in the 1950s as a gift from Paul and Bunny Mellon. The church also runs Upperville's Trinity Thrift and Boutique, which sells pre-owned treasures like designer bags and vintage artworks.

The town's most storied property is the Mellon's 4,000-acre estate, Oak Spring. Bunny Mellon was a landscape designer who helped First Lady Jackie Kennedy restore the White House Rose Garden. Her Little Oak Spring is a spectacular walled garden featuring mature trees, reflecting pools, colorful flower beds, and even a charming cottage brimming with straw baskets. Today, the property is part of the Oak Spring Garden Foundation and only opens to the public for ticketed events and special occasions, such as Virginia Historic Garden Week each spring. If you'll be around in June, another nearby event — the week-long Upperville Colt & Horse Show — can't be missed. Held since 1853, it hosts a wide range of equestrian show jumping and hunting competitions on the Grafton and Salem Showgrounds.

Upperville borders Loudoun County, which is best known as Washington DC's dazzling wine country. Within city limits, you can discover Slater Run Vineyards, a picturesque winery owned by a family that has been harvesting wines for 300 years. The 13 acres of vineyards produce several varietals, from light Pinot Gris white wines to full-bodied Cabernet Sauvignon reds. Sample them at the Slater Run Vineyards tasting room, open from Thursday to Monday.

On Route 50, in the heart of the Upperville Historic District, is destination restaurant Hunter's Head Tavern. The building dates to the mid 1700s, when it was built as a log cabin. Later, local businessman Joseph Carr bought the property. In 2001, communications entrepreneur Sandy Lerner purchased the building and reimagined it into Hunter's Head Tavern, which serves up delicious lunches, dinners, and an afternoon tea service. The beautifully restored interiors pay homage to the original structure via exposed wood beams, large fireplaces, and antique furnishings. The cuisine is elevated British pub fare with the meats sourced from Ayrshire Farm, a nearby property also owned by Lerner. Highlights at the tavern include chicken pot pie, steak frites, build-your-own burgers, and fish and chips. During the week, Hunter's Head Tavern also upholds the British tradition of classic afternoon tea service complete with homemade scones and finger sandwiches.

While there are no hotels in Upperville proper, the Welbourne Inn lies between Upperville and Middleburg. With history stretching back to the late 18th century, this elegant family-owned Colonial Revival mansion reflects the bygone gentility of another era. The seven guest rooms transport guests back in time with canopied beds, large fireplaces, and clawfoot tubs. Romantic touches abound and include weekend breakfasts served in the formal dining room alongside family silver and china.

For more modern accommodations, drive about 15 minutes from the Welbourne for the luxurious Salamander Middleburg. Set on a nearly 350-acre property, this five-star resort boasts 168 rooms and suites, two excellent restaurants, a pampering spa, and an equestrian center. While in Middleburg, don't miss a meal at the Red Fox Inn (Virginia's oldest restaurant), either.