To visit the deeply rural stretches of the Eastern Shore, you need to shun the artery highways — Rtes. 50, 301, and 404 — and instead poke along less-traveled local roads that connect Shore communities.

Case in point is Maryland Rte. 313, which originates at Rte. 54 in Mardela Springs and runs 75 miles north to Galena. It skirts Sharptown, Federalsburg, Denton, Greensboro, and Ingleside, and runs through El Dorado, Oil City, Goldsboro, Barclay, Sudlersville, Millington, and Massey.

Passing through five counties — Wicomico, Dorchester, Caroline, Queen Anne’s, and Kent — 313 runs through a quintessential panoply of the Eastern Shore. You’ll see small towns, countless acres of corn and soybean fields, drainage ditches, streams, and slow-moving rivers, Methodist chapels, crossroads stores, behemoth chicken sheds and grain dryers, historic sites, grade crossings for the local railroad, woods and woodlots, boat ramps, water towers, irrigation rigs looking like kids’ erector sets, and windmills, and crossings of the Nanticoke, Choptank, and Chester rivers. Your cup will run over.

There are numerous short side-trips as well, as follows:

Two miles east of 313 on Rte. 54 is the intersection of Charles Mason and Jeremiah Dixon’s survey lines of the border between Delaware and Maryland, circa 1767. Four granite stones mark this historic corner, also known as the Middle Point on the Trans-Peninsular Line.

During our nation’s shameful Jim Crow period, Booker T. Washington and Julius Rosenwald, a philanthropist and president of Sears Roebuck, built state-of-the art schools for African-American children across the South. A “Rosenwald School” — San Domingo School, also known as Sharptown Colored School — is just south of Sharptown, at 11526 Old School Road, off Cooper Mill Road. It closed in 1961, and is now used as a community center.

In Sharptown, a high modern bridge arches over the Nanticoke River, with a riverside park and boat ramp nestled underneath. The town has an annual firemen’s carnival.

Try to spot Methodist chapels at Wheatley Church Road, Dog Kennel Lane, and Chipman’s Lane. In downtown El Dorado, admire Lynn’s Market, a classic corner store at the intersection.

The Federalsburg by-pass crosses railroad tracks belonging to the Maryland-Delaware RR. This short line is headquartered in a restored railway station in Federalsburg, at 106 Railroad Avenue.

A few miles north of Federalsburg, look left to see the Eastern Shore Threshermen and Collectors Association, with ancient farm machinery on display.

As you near Denton — this drive’s halfway mark — take a breather in Martinak State Park, with miles of trails through acres of woodlands, as well as picnic tables, a boat ramp on the Choptank River, and rest rooms. 

North of Greensboro, turn right onto Red Bridges Road and drive a mile east on this dirt road to an upper reach of the Choptank. Because it’s shallow here, this was a spot in the 1830s and ‘40s for enslaved people on the run to wade across the Choptank in their dash  to Sandtown, just over the Delaware border. It’s now a stop on the Harriet Tubman Underground Railroad Tour, and a county park donated by the Christian family.

At Sudlersville’s single traffic light, look to your right to see the statue honoring the town’s favorite son and baseball hero, Jimmy Foxx. Known as “Double X,” Foxx was the second major leaguer to hit 500 home runs and was inducted into the Baseball Hall of Fame in Cooperstown, N.Y., in 1951.

Just before you reach Millington, turn into a public park at Unicorn Lake, a 43-acre impoundment that includes a state fish hatchery. The hatchery raises trout, largemouth bass, bluegills, and yellow perch for stocking and restoration. Note the fish ladder.

Massey is home to another M&D Railroad operation, with a locomotive barn and a switching yard; here its Northern Line splits to run either to Chestertown or to Centreville. Just two miles to the east on Rte. 330 is the non-profit Massey Aerodrome, billed as the “World’s Largest Flying Museum.” In non-pandemic times, the museum hosts an annual Chile Fiesta Fly-In. A World War II C-46 cargo plane is exhibited with pride.

This innovative system for receiving modern communications stands by the road west of Massey.

The road trip ends at the junction of Routes 313, 213, and 290 in Galena. From here, you can drive southeast to Chestertown, north to Elkton, or northeast to Middletown and Wilmington.

More Information:
Delaware’s state boundaries
Rosenwald School near Sharptown
Julius Rosenwald and the Education of African Americans on the Eastern Shore
Maryland-Delaware Railroad Company
Harriet Tubman National Historical Park
Massey Aerodrome

Cover photo: Sign upon entering Oil City, along Md. Rte. 313
Photos: All unattributed photos by the author