VT 58 begins at an intersection with VT 118 just south of the junction with VT 242 in the Franklin County town of Montgomery. VT 58 is town-maintained in Montgomery, running southeast as a two-lane concrete Hazen's Notch Road. The route parallels the Trout River out of the Montgomery Center neighborhood, converting itself to a dirt road as it runs southeast as it enters Hazens Notch, a local mountain in Montgomery. The route crosses through dense woods as a dirt road, turning southeast past residences through the densely wooded mountainside. Soon the residences give way to just woods as VT 58 reaches the Orleans County linealong the ridge of Hazens Notch. VT 58 crosses through the town of Westfield, entering Hazen's Notch State Park. Running along the southern ridge of the park, VT 58 bends southeast and leaves the park, but remains in the dense woods as a two-lane dirt road. The route crosses a junction with Monteith Road, which connects to nearby Balance Rock Road. Soon crossing into the town of Lowell, the dense woods around VT 58 begin to break as it leaves Hazens Notch, passing nearby Green Hill Road. Winding southeast, the town-maintained road reaches Buck Hill Road as the route becomes residential. Retaining the Hazens Notch Road name, VT 58 winds southeast at the East Branch of the Missisquoi River, paralleling the river and reaching the residential area of Lowell. In Lowell, the route reaches a junction with VT 100. At this junction, VT 58 becomes maintained by the Vermont Agency of Transportation rather than the town of Lowell. VT 58 drops the Hazen's Notch Road name, winding east through flat lands of Lowell. Turning northeast, the route becomes rural with no residences left until a few farmhouses near McAllister Road. The route winds northeast until Mitchell Road, where the route bends southeast for a jog. Turning northeast again, VT 58 begins an eastern wind through Lowell, crossing into the town of Irasburg. The route continues southeast through Irasburg, doing the same southeast-northeast jog it made in Lowell, climbing a ridge and past some large farms before reaching VT 14, where it passes a small housing development. At this junction, VT 58 and VT 14 become concurrent, running southeast through Irasburg and crossing the Black River near the junction with Under the Hill Road. Running along the riverside, VT 58 and VT 14 enter the center of Irasburg, where VT 58 turns east and off of VT 14. Running alongside the Black River, VT 58 passes the eastern end of Under the Hill Road, leaving the center of Irasburg. Now winding east along the riverside, VT 58 quickly turns away from the river in Irasburg, soon reaching a junction with U.S. Route 5. At this junction, US 5 and VT 58 become concurrent, running southeast as a divided highway as it enters a partial cloverleaf interchange with Interstate 91. Remaining a divided highway, VT 58 and US 5 turns northeast and enters the center of Orleans, where US 5 turns south. Paralleling the Barton River, VT 58 runs on Main Street, crossing the nearby railroad tracks. Now known as Church Street, VT 58 merges into East Street, changing to that name before turning southeast on the Willoughby River as Willoughby Avenue. Now in the town of Barton, VT 58 begins winding through some woods along the river, turning away from the river as Willoughby Avenue. Now reaching the hamlet of Evansville, the route enters the town of Brownington. At Hunt Hill Road, VT 58 leaves Evansville and winds southeast along the returned Willoughby River as Evansville Road. Remaining a two-lane road, the route is rural and runs through fields and dense woods until reaching a junction with VT 5A. This junction marks the eastern terminus of VT 58.
