Route 106 begins at a junction with
I-95 (exit 9) and
US 1 in the
East Side of Stamford as Courtland Avenue then turning right on Glenbrook Road. It runs parallel to the
New Canaan Line of the
Metro-North Railroad, heading northeast through the northwest edge of
Darien into the center of
New Canaan. In Darien, the road is known as Hoyt Street. Upon entering the town of New Canaan, the road changes name to Old Stamford Road, where it has an interchange with the
Merritt Parkway (at exit 13) as it heads into downtown New Canaan where it becomes Bank Street. It then continues north, briefly overlapping
Route 124 for then heads eastward as East Avenue and Silvermine Road into the town of
Wilton. In Wilton, the road is known as New Canaan Road and Wolfpit Road. Route 106 crosses the
Norwalk River as well as the railroad tracks of the
Danbury Branch then briefly overlaps
U.S. Route 7 and
Route 33 (0.18 miles) in downtown Wilton, then resumes its eastward journey along Sharp Hill Road then south along Chestnut Hill Road until its end at an intersection with
Route 53. ==History==