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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 1951, the southern part was redefined to follow Four Bridges Road to end at Route 83 instead of Route 190. This might have been to provide a more direct connection to downtown Somers.
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.