The Loneliest Road


From Cincinnati, US-50 follows surface streets through the warehouse and residential districts along the Ohio River before becoming a freeway for the quick drive east to Mariemont (pop. 3,464). Built in the mid-1920s as one of the nation’s first planned “Garden City” communities, Mariemont’s mock-Tudor downtown centers on the historic and comfortable Best Western Premier Mariemont Inn (6880 Wooster Pike, 513/271-2100, $140 and up), right on US-50. Across the street there’s a branch of the excellent local ice cream chain, Graeter’s. The sole surviving neighborhood of Mariemont’s original 1920s half-timbered arts-and-crafts homes is an easily walkable block to the southeast.

On the east edge of Mariemont, the legacy of old US-50 is celebrated right along the old highway at the popular Fifty West Brewing Company (7668 Wooster Pike, 513/834-8789), where good food and a range of local beers are served in a former roadside speakeasy. In summer, you can also rent kayaks or inner tubes for a leisurely float along the Little Miami River, on the south side of the highway, and the old railroad route is a rail trail running all the way from Cincinnati to Cleveland.

East of Mariemont, US-50 crosses the Little Miami River again at the scenic, 25-mph (40 km/h) town of Milford before racing east across 40 mi (64 km) of flat and sparsely settled farming country to Hillsboro. In Milford, there’s a Frisch’s Big Boy restaurant (840 Lila Ave., 513/831-0111), with a great old Big Boy sign, straight out of American Graffiti.


Hillsboro (pop. 6,527), 60 mi (97 km) east of Cincinnati and 40 mi (64 km) west of Chillicothe, is the biggest and busiest town along the way. Besides the Greek Revival landmark Highland County Courthouse, second oldest in Ohio, Hillsboro has a unique alcohol-related history: During Christmas in 1873, the town’s 13 saloons were closed down by one of the country’s earliest temperance movements, and more recently, late great country singer Johnny “Take This Job and Shove It” Paycheck did time in prison for shooting a man in Hillsboro’s North High Saloon. (Even more recently, that saloon was torn down to make way for a new city office building.

Serpent Mound

Across southwestern Ohio, US-50 winds past whitewashed farmhouses and broad cornfields flanked by low hills. The region also holds two fascinating remnants of the Mound Builder people who once lived here. Just west of the sleepy village of Bainbridge, heading 20 mi (32 km) south onto Hwy-41 (or following Hwy-73 south from Hillsboro) brings you to the Serpent Mound (800/752-2757, 9am-dusk daily, museum daily Mar.-Oct., Nov.-weekend before Christmas Sat.-Sun. $8 per car), which stretches in seven sinuous curves alongside a creek for nearly a quarter-mile (0.4 km). There’s a small museum on the site. To see the snake-shaped earthworks—the largest and finest effigy mound in the country—visitors climb up a turn-of-the-20th-century vintage lookout tower.

Another of these prehistoric sites, the Seip Earthworks, 3 mi (4.8 km) east of Bainbridge and 17 mi (27 km) west of Chillicothe, is over 200 ft (61 m) long and 30 ft (9 m) tall, surrounded by 10 ac (4 ha) of pasture. To prevent early farmers from plowing them into oblivion in the 1880s, many of these evocative monuments were purchased and preserved through the efforts of Harvard University archaeologists. Harvard owned the land for many years and later donated the sites to the state of Ohio.

Map of the Loneliest Road through Ohio.
Map of the Loneliest Road through Ohio.

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