North of Woodland, US 258 crosses Potecasi Creek and parallels the Northampton–Hertford county line north to Murfreesboro. The U.S. Highway joins US 158 east into Hertford County on its four-lane divided southern bypass of the town while the roadway continues straight as US 158 Business (Main Street). Southeast of the town, US 258 leaves US 158 and joins NC 11 on Beechwood Boulevard, which the two highways follow to NC 11's northern terminus at US 158 Business. US 258 leaves Murfreesboro on Virginia Boulevard, which crosses the Meherrin River and heads northeast through Como to the state line, where the highway enters Southampton County, Virginia. The U.S. Highway, now named Smiths Ferry Road, uses the General Vaughan Bridge to cross the Nottoway River a short distance north of its confluence with the Blackwater River to form the Chowan River.