Originally established in 1787 as “Powell Town” after Revolutionary War officer Level Powell, the picturesque town was renamed Middleburg due to its location midway between Alexandria and Winchester along the old Ashby Gap trading route.
The small town, which has gained popularity in recent years, has evolved into one of the most sought-after weekend escape destinations among Washingtonians seeking a change of pace from the District.
What makes Middleburg such a special destination?
While Middleburg, VA, has a rich history, there’s no single feature that makes it such a charming destination for a weekend trip from the District.
- Located in the midst of Virginia’s “wine country”, checking out vineyards in the area is a popular activity.
- With a massive equestrian culture, the town even hosts the oldest steeplechase race in the state.
- Home to one of America’s Oldest continuously operating inns, the Red Fox Inn & Tavern has been in operation since 1728
- Hosts the Middleburg Film Festival, which started in 2013 and has since become known as “Washington’s Sundance”, attracting major films and movie stars for premieres or early screenings.
- Possesses the only ‘Forbes Five-Star Spa’ in the state of Virginia: Salamander Resort & Spa.
- Famous for its annual ‘Christmas in Middleburg’ parade, featuring horses, hounds, carriages, and more.
- A lovely historic district featuring incredible architecture, lots of boutique shopping, and small town charm.
When is the best time to visit Middleburg, VA?
The best time, in our experience, is approaching now!
Middleburg is a beautiful sight year-round, but during the early fall, when the leaves begin to turn and the colder weather hasn’t fully arrived, it may be one of the most beautiful places in the world! (We’re not biased at all)
There are a few major events that you should be aware of if you plan to visit Middleburg:
- Middleburg Oktoberfest – Set to take place on September 20th this year.
- Middleburg Film Festival – Taking place around mid-October every year, in 2025 it will take place October 16th through 19th.
- Christmas in Middleburg – An annual event taking place in early December, this year the parade will take place on December 6th.
- Middleburg Spring Races – One of the oldest steeplechase events in the nation, the popular horse race takes place every spring.
These events are undoubtedly each a fun experience. If you want to see Middleburg at its most quaint and charming, you may want to avoid visiting around these dates to avoid crowds of other tourists or overpaying while in town.