South Mountain Gaps

Three times over South Mountain: from Smithsburg the route rides MD-77 to Foxville and MD-17 down through Wolfsville and Myersville to Middletown, crosses the ridge at Crampton's Gap through Burkittsville and Gathland State Park, follows MD-67 to Boonsboro and comes back north on MD-66 to Smithsburg. It's 52 miles of curves through creek valleys and farmland, on the passes of the 1862 Maryland Campaign. Watch for slick tar patches in heat or rain, and for walkers on Burkittsville's narrow main street in October.

South Mountain is the ridge where the Battle of South Mountain was fought on September 14, 1862, three days before Antietam, at three gaps. From Smithsburg the route rides MD-77 to Foxville, then MD-17 down through Wolfsville and Myersville, through creek valleys shaded by trees, to Middletown. From there it heads west to Burkittsville and climbs to Crampton's Gap, where Gathland State Park has the War Correspondents Memorial Arch, built in 1896 by George Alfred Townsend, a war correspondent, next to the Appalachian Trail.

Down the west side, MD-67 runs through Rohrersville to Boonsboro, and MD-66 brings the route back north to Smithsburg, crossing the ridge for the third time. The route avoids the stretch of I-70 that some versions of this loop use. The pavement is generally good, with slick tar patches in heat or rain, and Burkittsville's main street is narrow, with lots of walkers in October.