Browse among the delightful array of quaint shops and inns. There are approximately 670 people currently residing in the town. Established in 1787 by Revolutionary War Lieutenant Colonel and Virginia statesman, Levin Powell, he purchased the land for Middleburg at $2.50 an acre from Joseph Chinn, first cousin to George Washington. Previously called "Chinn's Crossroads," Powell chose the name Middleburg because of the town's location midway between Alexandria and Winchester on the Ashby Gap trading route (now Route 50).

Since the 1730s, Middleburg had been a staging point for weary travelers along the Ashby Gap Road. The legacy of the colonial era continues today at Middleburg's charming inns that provide first rate accommodations to visitors from around the world. There are several inns located within the corporate limits, including the historic The Red Fox Inn and Tavern and Middleburg Country Inn.  The Red Fox Inn and Tavern is billed as the "oldest original inn in America". The Red Fox Tavern was a meeting spot for Confederate Colonel John Mosby and his Rangers. A century later, President Kennedy's press secretary, Pierre Salinger, held press conferences at the Red Fox in the Jeb Stuart Room. In 2013, The Salamander Resort and Spa opened to offer travelers another type of stay; accommodations like none other in this area. 

Across the street is another gracious reminder of the past - the Windsor House Inn, circa 1824. During the Civil War, it was known as the Colonial Inn; and, was run by Catherine Broun. Although Catherine sympathized with the South, she generously served meals to Union troops at the inn as well when they occupied Middleburg in 1862.

After the turn of the century, Middleburg began welcoming a new wave of visitors that descended on the town for foxhunting and steeplechasing. The charming village soon earned a reputation as the "Nation's Horse and Hunt Capital," attracting prominent visitors from across the United States.
Serving as a host community for more than 250 years, it is no surprise that Middleburg has developed such a high concentration of fine inns, shops and restaurants.

Middleburg was recognized in 2008 for its historic preservation efforts by being designated a Preserve America Community by then-First Lady Laura Bush.  


2019 is set to be a pivotal year for the Middleburg community, our rural way of life and all of Loudoun County.  This November will see a unique election dynamic as we choose our next Delegates, our next Senators, and more importantly, the next Loudoun County Board of Supervisors - all of whom are up for election/re-election.  The campaign cycle is getting into full swing and this creates an opportunity for us all to be heard more than normal - by our vote.  It is an incredibly important time for us to engage in the political process and ensure that the county representatives we select reflect our vision for our community and our County.  Central to this vision will be the direction the Board takes this summer when they vote on the new Comprehensive Plan and how the candidates plan to implement it after the election.  Read more ....

Photo courtesy of Justin Kriel Photography

Click on the calendar icon to go to the Town of Middleburg's Calendar


The Town of Middleburg, a dynamic and historic small town in Loudoun County, Virginia, has an immediate opening for a full-time Treasurer.  This key leadership position is responsible for financial planning and anaylsis, budgeting, cash management, accounting and financial reporting, debt management, procurement, and other municipal finance-related tasks. Examples of activities include:... 

Town of Middleburg, VA

 from Mayor Bridge littleton:


Click on the picture of Barkley
to see a pdf document with very important tips on keeping your dog safe and healthy in Middleburg.

Welcome to Middleburg


The Middleburg Planning Commission has prepared a draft Comprehensive Plan and is committed to ensuring that it reflects the desires of the community that were relayed during earlier public input sessions and surveys.  To that end, the Commission welcomes and encourages comments on the Plan and invites the community to participate in a number of ways:

  • review the May 14, 2019 version of the draft Plan posted here and submit any comments you may have to Deputy Town Administrator Will Moore at 

  • attend a PUBLIC OPEN HOUSE on Wednesday, May 29 at 6:00 pm at The Hill School at 130 S. Madison St (in the Sheila C. Johnson Performing Arts Center)  

  • attend and comment at the Commission's public hearing on the draft Plan on Monday, June 17 at 7:00 pm in the Town Office at 10 W. Marshall Street.