The three towns had previously maintained the highway with support from the state for construction and maintenance, including reconstruction along several segments in the 1940s.

The two-lane highway crosses Mill Brook, which it parallels for its entire length, and enters the town of West Windsor.

VT 44 ascends from the valley of Mill Brook and passes the entrance to Ascutney Mountain Resort shortly before entering the town of Windsor.

VT 44 passes the Ascutney Mill Dam Historic District before it curves east onto Union Street.

The highway crosses Mill Brook twice more in the downtown area and passes by the historic residential NAMCO Block before reaching its eastern terminus at US 5 and VT 12 (Main Street) just north of the American Precision Museum at the historic Robbins and Lawrence Armory and Machine Shop.

[3] The first hard-surfaced stretch of what was to become VT 44 was created at an unknown time before 1950 along Ascutney Street in the Windsor town center.

North of the Weathersfield–Windsor town line, VT 44A crosses over I-91 and provides access to Mount Ascutney State Park, which includes a toll road that ascends the mountain.

[4] The 1927 Bureau of Public Roads–Vermont State Highway Department report indicated the unnumbered road along the east flank of Mount Ascutney had an untreated gravel surface.