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In the 1920s, State Highway 104 followed today's Route 17 between Glastonbury Center and today's Route 66 in Portland.
In 1932, Route 104 was commissioned as an 8.40-mile route from US 1 to the New York state line:
The designation of nearby Route 137 was chosen to continue a New York state route designated in 1930. However, Long Ridge Road was never marked as a state route in New York. The Route 104 choice is Connecticut's.
USGS maps in 1947 and 1951 appear to show Route 104's southern segment shifted from Bedford Street to Summer Street. However, today these streets are an opposing one-way pair; if that was true decades ago, then Route 104 traffic would have used both.
At some point later, Route 137 was extended south along Washington Blvd. to US 1. Route 104's southern end was truncated to Route 137, so now Route 104 extends along Long Ridge Road only.
Also, possibly around 1976, a realigned 1.3-mile section of Route 104 opened in northern Stamford. The older section is now Old Long Ridge Road.
Circa 2008, the small, tight 4-ramp interchange at the Merritt Parkway was reconstructed. The two loop ramps remain; but the diagonal ramps were lengthened, and a new ramp from Route 104 northbound to the Parkway northbound was added.
In 1963, an assistant chief planner at the state highway department announced in Darien that "three major expressways" were planned in the area in the "foreseeable future". These were:
There were a few area proposals for a north-south highway between Stamford and Pound Ridge, N. Y. or Bedford, N. Y. In 1956, the Westchester Planning Department proposed a high-speed "Stamford - Bedford Village Road" between Routes 104 and 137, though noting that the route "might be cancelled." In 1969, Westchester County proposed a freeway upgrade to Route 137.
No north-south freeway in Stamford was built (I-95 and Route 15 are locally east-west), and no such plans are active now.
Does Route 104 perform the noble service of segregating the wealthy from the merely affluent, or old money from new? Hartford Courant columnist Denis Horgan fired this salvo in 1999 (see "sources"):
Put aside the trifling truth that there is barely a person west of Route 104 who gives a hoot for the rest of Connecticut or who would tell us that our car was on fire in the parking lot or that our necktie was dangling into the soup. Set apart the passing reality that those down in Connecticut's tail consider the remainder of the state to be a congregation of riffraff and field hands.