Sideling Hill has long challenged travelers as an ancient route that people pushed across, around, and finally through. First appearing on a 1755 map as “Side Long Hill,” it was a steep and dangerous climb. When frontiersman Thomas Cresap moved up the Potomac Valley, he hired local Indians to widen the trail over the mountain for his wagons. During the heyday of the National Road, stagecoaches crashed and passengers were killed on the slope near Hancock. Even throughout the 1930s, the 40 miles to Cumberland on US 40 was still considered a long, hard trip over five mountains, including Sideling Hill. In the 1980s, construction of I-68 finally tamed this 350 million-year-old ridge with a 4½ mile long, 380 foot deep, and 200 foot wide cut. After two years and $20 million of blasting, the first motorists drove through the cut in August, 1985, and the deepest road cut in Maryland history had moved 4.5 million cubic yards of rock and dirt.