Middleburg, Virginia

By VI | Disclosure: I use affiliate links

Rostislav Sedlacek/stock.adobe.com

When I’m craving a weekend of elegance, rolling hills, and good wine, I head to Middleburg—and I think you’ll fall for it just like I did. Nestled in the heart of Virginia’s Hunt Country, this town has a peaceful, polished feel that’s perfect for unwinding. I’ve strolled boutique-lined streets, sipped wine at scenic vineyards, and even caught glimpses of riders on horseback in the countryside. Whether you’re here for a spa day or a quiet escape, Middleburg wraps you in charm and refinement from the moment you arrive.

Best Time to Visit

I love visiting in spring (April–June) or fall (September–November)—that’s when the landscapes come alive with blooms or foliage, and the weather is ideal for wine tastings and countryside drives. Summer is a great time for vineyard picnics and festivals, while winter brings cozy inns, fireplaces, and twinkling holiday lights that turn the town into something out of a postcard.

How to Get There

If you are traveling by car: I usually drive out on U.S. Route 50—it’s an easy and scenic trip about 1.5 hours west of Washington, D.C. You’ll pass through charming backroads as you approach town.
By Plane: I fly into Washington Dulles International Airport (IAD) when coming from out of town. From there, it’s a relaxing 40–45 minute drive into the heart of Hunt Country.
By Train: If you’re thinking about rail, I’ve used Amtrak to Manassas or Vienna before. You’ll still need a car or ride from the station, but it’s a comfortable way to get close.