Route 106 winds through some tony suburbs in Fairfield County, intersecting four major highways in the area. Near its northern end in Wilton, Route 106 participates in a triple overlap with US 7 and Route 33.
Updated Aug 28, 2024
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In the 1920s, State Highway 106 followed today's Route 81.
On Jan. 1, 1932, the old Route 106 was commissioned as Center Street, a 2.47-mile east-west connector between Route 58 and Route 59 through Easton Center. The recommendations in the state highway reclassification of 1961 included removing Center Street as a state highway, and instead including Westport Road.
In 1962, Center Street was turned over to the town. (Westport Road is now part of Route 136.)
In 1963, Route 106 was moved to its approximate modern location. The old and new Route 106's are about 8 miles apart; imagine having returned to the area after being away only a few years.
Parts of the second Route 106 were already state-maintained, but not yet signed:
The recommendations in the state highway reclassification of 1961 included a secondary route from Stamford to Wilton via New Canaan. A few segments were briefly made state roads in 1962, before Route 106 was designated in 1963:
The 1963 alignment of Route 106, incorporating SR 747/748/749, was 15.26 miles:
In the early 1970s, Wilton officials started advocating for a shorter alignment for Route 106, along Wolf Pit Road; reasoning the new route would be simpler, use better roads, and help decrease traffic on US 7. In 1993, discussions progressed; the town would need to improve Wolf Pit Road, including two bridges, before the state would be willing to take it over.
In 1998, the stars aligned with town and state satisfied, and Route 106 is now 0.89 miles shorter, using Wolf Pit Road and Sharps Hill Road.
Route 106 was featured in a November 2006 promo for the NBC sitcom "The Office."
Scene: Dunder Mifflin Co, Stamford office
Andy: Big Tuna! What's the best way to get from Darien to Wilton?
Jim: Well, I'm still getting to know the area, but, uh... Route 106.
Andy: Hup! [Laughs derisively] Sure, if you want to get stuck in traffic all day! [Pauses] If you don't know something, Big Tuna, it's OK to just say "I don't know." You don't need to impress me.
Andy's right: the most direct route is I-95 and US 7... free-flowing routes that bypass all that Route 106 traffic :-)