CT 106 is a north/south route extending from Stamford to Wilton. It begins at East Main Street (US 1) in Stamford, near exit 9 of the Connecticut Turnpike (I-95), and runs north along Courtland Avenue. About a mile to the north, Courtland Avenue ends at Glenbrook Road in Glenbrook. CT 106 turns east onto Glenbrook Road, which crosses the Noroton River and changes names to become Middlesex Road. After a few blocks, CT 106 turns north again onto Hoyt Street. A few miles to the north, Hoyt Street changes names to become Old Stamford Road and has an interchange with the Merritt Parkway (CT 106). About a mile north of the parkway, Old Stamford Road curves to the east to become Bank Street, which ends at South Avenue (CT 124). CT 106 is multiplexed with CT 124 through New Canaan along South Avenue, Cherry Street, and Main Street. In the downtown area of New Canaan, it splits off from CT 124 and turns east again onto East Avenue, which extends for about half a mile to New Norwalk Road (CT 123). It continues east as Silvermine Road for about a mile and a half. Then, it turns north for one block on Valley Road and then east again on New Canaan Road. New Canaan Road in turn becomes Wolf Pit Road, which ends at Danbury Road (US 7) in Wilton. CT 106 is multiplexed with US 7 for one block to the north and then turns northeast onto Sharp Hill Road. After about a mile, Sharp Hill Road ends and CT 106 turns southeast onto Chestnut Hill Road for about half a mile to end at CT 53. The entire length of CT 106 is a two-lane undivided road.
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