I came across this newsreel footage of the Third Avenue Elevated Railway in New York, from just before it was torn down.
Built in 1875, the Third Avenue EL was the last elevated railroad in New York City. Service in Manhattan ended in the 50s, but portions remained in use in The Bronx until the 70s, according to Wikipedia. The decline in service and ending of the line does not seem to be because of demand — the article points to real estate interests.
According to Gotham Center, 25 million people rode the EL in 1954, its last year of operation. The author, Lawrence Stetler, went on to say:
New York lost a well-functioning, if timeworn, transit resource that was in need of rehabilitation but not demolition when it took down the Third Avenue El. To this day, people who live or work on the East Side are forced onto the perennially overcrowded Lexington Avenue Subway, the only rapid transit line running the length of the east side of Manhattan, or crowded, often late buses.
The City promissed the residents of the East Side a subway line, but construction on the Second Avenue Subway didn’t begin until 1972, halted in 1975 and only two out of a proposed 8.5 miles are currently under construction at enormous cost. Money was voted in the early 50s when ending service on the EL was decided, but it was spent on other things.
What does public transit have to do with the free market?
Subways, passenger trains, commuter trains, elevated lines and light rail were all built succesfully by private enterprises in 19th century America. They came to be under the control of transit authorities because early 20th century progressives, who also gave us lobbyists and the revolving door between government and industry, decided that transit fares should not excede a nickel. This was probably fine in 1910 or whenever (although, as Harpo and Groucho Marx both noted in their autobiographies, even five cents could be out of reach of a lot of people), but by the time of the Depression was completely inadequate for either operating expenses or capital costs and by 1950 transit services had been snapped up by municipal governments at bargain basement prices. Many of the lines were sold for scrap and replaced with bus services (sometimes there was lobbying from automobile companies, giving rise to the legend of the Great American Streetcar Scandal).
The main problem, from a free market perspective, with the transit firms, was that they got their routes not by buying the rights to them from whoever the owners happened to be, but through franchises granted by the City or the state. Homesteading rapid transit routes probably would have prevented some of the problems that continue to be associated with transportation — namely high fixed costs (competing railroads in the 19th century went through a neverending cycle of investment, price war, cartelization, treachery and bankruptcy). Homesteading out air or underground rights probably would have resulted in firms cooperating to profit from the routes instead of the railroad wars that resulted in no one profiting and the infrastructure falling into ruin.