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Among road enthusiasts, Route 182 may be best known as the only remaining 3-digit signed state route with a signed alternate: Route 182A. It follows the former Old North Road, which in pre-Revolutionary days was the path settlers followed from Hartford into northwestern Connecticut. (In other words, it may have predated US 44 to the south.)
Commissioned in 1932 from the old State Highway 327, Route 182 originally incorporated what is now Route 182A. In 1940, Route 182A was created, and Route 182 was moved to where it is now.
Smith Hill Road, maintained by the town of Colebrook, connects Route 183 (across from the Route 182A terminus) to Route 8 (across from the Route 20 terminus). In 1961, two state senators submitted a bill to add it to the state highway system. The state highway department was conducting a Route Reclassification at the time, which would lead to many roads changing hands between town and state maintenance.
In 1962, Smith Hill Road was slated to be included as a state road. However, the segment of Stillman Hill Road (Route 182) between Route 182A and Route 183 would be turned over to the town. The probable route number change would eliminate Route 182A and extend Route 182 along its alignment onto Smith Hill Road.
In 1962, the town took a vote on the issue. Some residents were concerned that Smith Hill Road, 18 feet wide, would be expanded to match existing Route 182, which was 36 feet wide, leading to property loss. In any case, Route 182 was never changed, and Smith Hill Road remains a town road.
If the change had gone through, Smith Hill Road would have been a natural extension of Route 182 to Route 8. However, what if Route 20 had been extended the other direction? It could have replaced Route 182 for its entire length, leading to US 44.