Leesburg is in the heart of Virginia wine country. If you want to explore other local wineries, we recommend Cana Vineyard, Creek's Edge Winery, and Bluemont Vineyards, all 20-30 minutes from Leesburg. Loudoun County also has guided wine tours. For history buffs, the Winery at Bull Run is a 30-minute drive from Leesburg and is located near the Manassas National Battlefield Park where the first battle of the Civil War was fought. They have great wines and also display cool Civil War artifacts found on vineyard grounds.
Leesburg is known for its wineries, but it is also a historic Virginia town with plenty of shops, restaurants, bars, art galleries, boutiques, and museums. Our favorite restaurants are King Street Oyster Bar and Tuscarora Mill.
If you're looking for a good hike within 20 mins of Leesburg, our two favorite hikes with great overlooks are Raven Rocks and Bear's Den, both along the Appalachian Trail. Raven Rocks: https://www.hikingupward.com/ovh/ravenrocks/ Bear's Den: https://www.visitloudoun.org/listing/bears-den-overlook/2684/ Great Falls Park is 45 minutes from Leesburg and has a giant waterfall along the Potomac River - definitely worth a trip if you have time: https://www.nps.gov/grfa/index.htm Shenandoah National Park is an hour from Leesburg if you're looking to venture into the depths of the Appalachians.
If you're near Dulles and you're a nerd, you may as well check out the Air & Space Museum Annex (Udvar-Hazy Center). This is the big airplane hangar with the airplanes you can go in, and also the space shuttle - much cooler than the Air & Space museum on the National Mall although that one's cool too :)
We encourage you to check out DC while you're in the area! This time of year the National Cherry Blossom Festival will be underway, which means cherry blossom-themed events, art shows, parades, etc. All Smithsonian museums and the National Zoo are free to enter. We recommend the National Museum of Natural History (the most visited museum in the world!) but we might be biased. **Driving and parking will be difficult downtown DC due to tourist activity. We recommend taking the DC Metro where possible.