US 258 meets the western end of SR 189 (Quay Road) before reaching its diamond interchange with US 58 (Southampton Parkway) south of the independent city of Franklin. US 258 joins US 58 on a four-lane freeway heading east while the roadway continues north into the city as US 258 Business (South Street). US 258 and US 58 head southeast through a widely spaced partial cloverleaf interchange with SR 714 (Pretlow Street) before crossing the Blackwater River into the city of Suffolk. East of the river, the U.S. Highways have a partial cloverleaf interchange with SR 189, which joins US 58 heading east toward Norfolk while US 258 exits the freeway and heads north, becoming Great Mill Highway on entering Isle of Wight County southeast of Franklin. When Great Mill Highway continues north toward an industrial area on the east side of Franklin, US 258 veers northeast on Camp Family Highway, crosses over Norfolk Southern Railway's Franklin District, and meets the northern end of US 258 Business at its intersection with US 58 Business (Carrsville Highway) just north of its grade crossing of CSX's Portsmouth Subdivision rail line and just south of Franklin Municipal-John Beverly Rose Airport.