Shenandoah National Park and the Rapidan Wildlife Management Area are located in the county as well as a portion of the famous Skyline Drive. Popular hiking destinations include Old Rag Mountain and White Oak Canyon.

Four wineries call Madison County home - Prince Michel and Sweely Estate are two larger producers, while Castle Gruen and DuCard Vineyards (together with Sharp Rock Vineyards just "over the line" in Rappahannock County), are boutique, family-run operations in gorgeous locations. Also check out the Foothills Scenic Wine Trail with info about wineries and attractions along the road.

Graves Mountain Resort in Syria offers apple pickin' as well as banjo pickin' with its popular festivals, such as the Graves Mountain Bluegrass Festival every May and the Apple Harvest Festival every October.