VT 44 begins at an intersection with VT 106 north of the hamlet of Felchville in the southeastern part of the town of Reading. The two-lane highway crosses Mill Brook, which it parallels for its entire length, and enters the town of West Windsor. VT 44 crosses Willow Brook near
Best's Covered Bridge and Mill Brook again near the
Bowers Covered Bridge. The highway crosses Mill Brook twice more in the town as it curves around the northern flank of Mount Ascutney. VT 44 crosses Beaver Brook while passing through the village of
Brownsville. VT 44 ascends from the valley of Mill Brook and passes the entrance to
Ascutney Mountain Resort shortly before entering the town of Windsor. East of the town line, VT 44 veers away from Mount Ascutney at its oblique intersection with VT 44A (Back Mountain Road), which continues southeast along the flank of the mountain and heads toward I-91. VT 44 descends back into the valley of Mill Brook and crosses the stream immediately before it passes below I-91 with no access and curves north with the stream. The highway enters the urban area of Windsor along Ascutney Street. 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. The east leg of the intersection is Bridge Street, which leads to the
Cornish-Windsor Covered Bridge across the
Connecticut River and into the state of
New Hampshire. The
Vermont Agency of Transportation maintains VT 44 west of VT 44A, and the town of Windsor maintains the route east of VT 44A. ==History==