Boonsboro, Md The Other Annapolis Annapolis Rock
From a parking area near Route 40, follow the blue-blazed spur to the white-blazed Appalachian Trail and go north. After this ascent, the shaded path levels out and runs along the ridge of South Mountain for a little under two miles. Gorgeous ferns line sections of the path. A blue-blazed connector turns west down to the overlook atop Annapolis Rock, with views of verdant mountains and Greenbriar Lake. The cliff is popular with climbers. For more, see localhikes.com. Make it Longer: Return to the Appalachian Trail and continue north a mile to the Black Rock Cliff overlook.