In 1728, Joseph Chinn built a tavern out of the local fieldstone at the half-way point between Alexandria and the frontier town of Winchester, Virginia, along what is today known as the John Mosby Highway. The territory around Mr. Chinn's Ordinary, as it came to be called, was part of the vast estate of Thomas, sixth Lord Fairfax and Baron Cameron, an eccentric bachelor who preferred his log cabin on the Shenandoah to the celebrated social responsibilities of his London palace on the Thames. Chinn's Ordinary soon became a popular stopping-point for traveling colonists, and around 1748 was visited by an enthusiastic young surveyor named George Washington.

In 1787, Chinn's Crossroads and fifty acres were sold to the newly chartered town of Middleburg for $2.50 an acre. Middleburg was so named because it lay a day's ride by coach or on horseback from Alexandria and another day's ride from Winchester in the Shenandoah Valley. Thus being in the "middle," the village provided the overnight resting stop for travelers making the 70-mile overland journey. While Middleburg prospered and grew in reputation as the nation's foremost area for fox hunting, thoroughbred breeding, and horse racing, Chinn's Ordinary remained the focal point for the area's social and economic activities. In 1812, Chinn's Ordinary was christened the Beveridge House. It was enlarged to 35 rooms and an extensive new wine cellar was added.

During the Civil War, the Beveridge House was often used by the Confederates. Most notably, it was where General Jeb Stuart met with Colonel John Mosby and his famous Mounted Rangers. And at the beginning of the Gettysburg campaign, as fierce cavalry battles raged around Middleburg, the inn served as both headquarters and as a hospital for the Confederates. While strategy was planned upstairs in what today is the Jeb Stuart Room, wounded soldiers were cared for in the tavern rooms below. The pine service bar, which is in use today in the Tap Room, was made from the field operating table used by an Army surgeon who served with General Stuart's cavalry.

In 1887, the Beveridge House was renamed the Middleburg Inn, and continued to offer fine food and accommodations in the best Virginia tradition.

In 1937, a local citizen saved the venerable building from the wrecking ball and renamed it the Red Fox Inn, as it is known today. The historic structure was remodeled with the help of a then young local architect, William Dew, who still lives and works in the village.

Throughout the years, the Inn has been used for many notable events and by many well-known people and has remained a popular destination for anyone who seeks a romantic hideaway in the heart of the hunt country. The Jeb Stuart Room, for example, served as the stage for a rare press conference by President Kennedy and as a meeting room for hopeful Democrats hosted by Ambassador Pamela Harriman, a local fox-hunting resident; Elizabeth Taylor often graced the Tap Room both during the courtship and after her marriage to a local gentleman, Senator John Warner; and the lovely and kind Jacqueline Kennedy Onassis frequently stayed at the Inn during fox-hunting holidays each fall. Today, film and music celebrities are often seen in the hotel and dining rooms.

The Red Fox Inn is on the National Register of Historic Places and the Virginia Landmarks Register.

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