US 258 continues northeast as Walters Highway through the hamlet of Walters to the town of Windsor, where the highway is named Prince Boulevard, has a grade crossing of Norfolk Southern's Norfolk District rail line, and intersects US 460 (Windsor Boulevard). The U.S. Highway continues north as Courthouse Highway through the county seat of Isle of Wight to the town of Smithfield. US 258 enters the town as Main Street before joining SR 10 on the town's bypass; Main Street continues as US 258 Business. The two-lane bypass has a diamond interchange with Fairway Drive, then crosses Cypress Creek and collects the northern end of US 258 Business, which runs concurrently with SR 10 Business on Church Street. US 258 and SR 10 continue southeast on four-lane divided Benns Church Boulevard to Benns Church, where US 258 leaves SR 10 and joins SR 32 on Brewers Neck Boulevard. The U.S. Highway and state highway follow that boulevard to Carrollton, where the highways join US 17 on Carrollton Boulevard. The three highways curve northeast and cross the James River on the James River Bridge.