The Bear's Den Rural Historic District contains a rare collection of well-preserved historic resources from the late 19th century to the mid-20th century that were constructed primarily by wealthy Washingtonians who were drawn to the seclusion and cooler climate of the area. While there is variety in the style of the buildings, which are primarily dwellings and their outbuildings, they share similar characteristics. They use native materials, such as greenstone and wood, and were sited so as to take the best advantage of the breath-taking views of the Shenandoah or Loudoun valleys from their wide, often wraparound porches. While rustic in their general character, these houses have detailing representative of popular architectural styles of the period which gives them an air of sophistication.

Bear's Den Rock, the famous overlook off the Appalachian Trail for which the historic district is named and which offers some of the most spectacular views of the Shenandoah Valley in the state, is located near 18383 Blue Ridge Mountain Road. - NRHP, 15 April 2009