Route 155 was created in 1933 or 1934. The only alignment change since then: the segment of Randolph Road between modern Route 9 and Saybrook Road (old Route 9) became a city street in 1962.

2004 proposal: extend Route 155 across CT River?

At a 2004 forum covering traffic issues in Middletown, State Rep. Joseph Serra brought up an interesting idea: building a new east-west bridge across the Connecticut River at Randolph Road / Route 155.

Either a new road (Route 155 extension?) would continue north to Route 66, or the road would connect to Route 151 in East Hampton. There were no details on which alternative was contemplated.

The new bridge would allow eastbound traffic from Route 9 to skip Middletown congestion and relieve traffic on the Arrigoni Bridge carrying Routes 17 and 66. That would make upgrading the overworked 1938 bridge easier.