F-Line to Dudley
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^ This is kind of a non sequitur, no? Logan Airport becoming Boston's international is a consequence of decisions made in the 1950s. To tie that to light cycles and pairing them as evidence of chronic failure to think critically on the part of regional city planners is... not effective. Not saying your claim is wrong, just pointing out the relative weakness of this argument.
Earlier than that. Commercial passenger flights have been operating out of there since 1927, international flights since 1946. Major landfilling of the Harbor Islands to add the runways that made it the huge hub it became all happened 1943-47. It was even the first airport in the U.S. to have a rapid transit stop when the Blue Line was extended in '52.
How far back do we want to retroactively apply the "piss-poor" planning tag for not being able to foresee a rush hour on 1A? Logan had already gone "modern" before there was such a thing as planes with pressurized cabins. If we go any earlier you'd have to slag off on 118 trolley out of Maverick being too slow to catch a boarding on the open-cockpit biplane piloted by some ex-WWI daredevil who regales passengers between nips of whisky of claims that he was the guy who shot down the Red Baron over France. Planning can only predict as far as a future that is plausibly reliable to predict. If the airport were placed anywhere else in 1930-something, would we have done any better at predicting traffic over the subsequent 80 years? Vanishingly unlikely. That other site would have its own gripe list of coulda/shoulda/wouldas just as far beyond anyone's ability to predict.