Raven Rocks (5 mi, hard) and Bear's Den (1.6 mi, easy) are great hikes located just off the highway in Bluemont, Virginia.
We love Tuscarora Mill and Shoes, Cup and Cork in Leesburg, Clyde's Willow Creek in Ashburn, or Dolce and Ciabatta Bakery for a casual bite.
Leesburg is surrounded by many excellent wineries. Stone Tower and Casanel are two great options.
Downtown Leesburg is filled with cute shops, galleries, and restaurants.