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Route 186 is a short highway that nonetheless crosses a state line, and intersects two other highways in Massachusetts that cross back into Connecticut. The Bay State terminus is a seven-way intersection in central East Longmeadow; the four-way intersection in the Somersville southern terminus is more conventional.
Commissioned in 1932, Route 186 has undergone one location change (which was later reversed). The original alignment (the same as today's) started at Route 190 (at the time, called Route 20) at Somersville and followed Hall Hill Road to the state line.
In 1939, Massachusetts designated a matching Route 186 extending from the state line to East Longmeadow.
In January 1951, a state bill was introduced to add Four Bridges Road, leading from Route 83 to Hall Hill Road (Route 186), to the state highway system. Later in 1951, the southern part was redefined to follow Four Bridges Road to end at Route 83. The segment of Hall Hill Road continuing to Route 190 was turned over to the town.
Perhaps Somers officials wanted both old and new Route 186 as state highways; or they might have preferred a more direct connection to downtown Somers from Massachusetts.
The recommendations in the 1961 Route Reclassification included dropping Route 186 from the state highway system. Instead, it was retained; and in 1962, was moved back to its original location.
Four Bridges Road is no longer state maintained.