Town Hill Overlook marked a high point along the old National Road where the long, winding ascent of Town Hill, though reaching a height just beyond Sideling Hill, was easier to cross, even as early automobiles still struggled with the steep grades and tight turns. Around the turn of the twentieth century, this was a largely uninhabited stretch, wild and beautiful, with clear air and more bridges than people. Travelers could find welcome relief at a service area with a gas station, a restaurant serving home cooked meals, and lodging. From the overlook, visitors could see three states and seven counties, and in the 1920s, with apple orchards surrounding it, tourists began calling the area the Beauty Spot of Maryland. The Town Hill Hotel was among the first places along the old National Road to cater to twentieth-century pleasure travelers, and similar hotels were soon placed atop Sideling Hill, Green Ridge, Polish Mountain, Martins Mountain, Big Savage, and Negro Mountains. The Town Hill Hotel is the only 1920s hotel in this area still operating today.

Photo: Devry Becker Jones

Little Orleans, Maryland · USA