Downtown Leesburg is one of our favorite local spots - a quaint downtown area with local boutiques, coffee shops (go to Goosecup!), great restaurants (King Street Oyster Bar and Rebellion Bourbon Bar + Kitchen are our favorites), wine bars, and historic charm + free parking!
Middleburg, VA is quintessential Virginia Hunt Country — a charming, historic village known for its rolling countryside, horse farms, and timeless small-town feel. Just a short drive away from Leesburg/Ashburn, with boutiques, cafés, wine tasting rooms, and a beautiful main street it’s the perfect spot to wander for a few hours! Free street parking is available down main street.