Route 58 begins at Route 28 on the Rochester–Wareham town line.[2][3] The route follows the town line for approximately a tenth of a mile before being wholly in Wareham. It then crosses I-495 before clipping the corner of Middleborough and re-entering Wareham for a short while before finally entering Carver. For the first 1.4 miles (2.3 km) of this route, none of the town line changes are signed.
The route turns northward through the town of Carver, passing Edaville Railroad and the King Richard's Faire grounds as well as the center of town. In North Carver the town intersects U.S. Route 44 just west of where that route becomes a four-lane freeway. Before the freeway was completed, the route had a short concurrency between its current exit ramps to Plymouth Road, where the route continued eastward to Plymouth. Route 58 then passes through the small town of Plympton and into Halifax, where it intersects Route 106. It then passes between the East and West Monponsett Ponds before crossing into Hanson.
When first established in the late 1920s, Route 58 went from Wareham to Canton ending at Route 138. In Abington, instead of heading straight at the intersection with Route 123, the route went right, running concurrent along Centre Avenue until Spring Street where it turned left and crossed into Weymouth on Union Street. Route 58 then followed what would be the 1931-1959 routing of Route 128 through Weymouth (Columbian Street), Braintree (Columbian Street, Grove Street, Franklin Street, and West Street), Quincy (Blue Hill River Road), Milton (Blue Hill River Road, Hillside Street) and Canton (Royall Street) before ending at Route 138. In 1931, with the establishment of the new path of Route 128 from Dedham to Hingham, Route 58 was truncated back to Main Street in Weymouth continuing its modern path north of Route 123 to end at what is today the intersection with Route 18.[4][5]
Route 28 on the Rochester–Wareham town line
Route 18 in Weymouth
