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.
In 1963, Route 106 was moved to its approximate modern location; Center Street was returned to the town. These two Route 106's aren't very far apart; imagine having returned to the area after being away only a few years.
In 1998, Route 106 was moved slightly. From the intersection of Belden Hill Rd and Wolf Pit Rd, it originally followed Belden Hill Rd north to Route 33, then paired with routes 7 and 33 before continuing easterly on its own. Now Route 106 continues east along Wolf Pit Road to routes 7 and 33, then following them northbound a short distance before turning east as before. As a result, Route 106 is 0.89 miles shorter than before.
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.