The original path curved away from the new Nutt MECS Center at Trinity, but even engineering bears won’t follow a path that leads in the wrong direction:

An old story has it that [name of administrator] at [name of new college] had the architect remove all but the most obvious walking paths from the new campus plans. After the first year passed, then they paved the routes that people actually used.
Vassar College has a good example of that design in the residential quad:

But even they won’t slash diagonals across a lawn just for students:

At Metro State College in Denver, they removed a street between several buildings and landscaped it. Not an urban legend, they really did leave out all sidewalks until the natural paths killed the newly planted grass, and then put the sidewalks there. It was cool when they were tearing up the old street to find horse shoes and other artifacts. Hard to imagine that the road was originally built for wagons and not cars.
The Mohawk River goes through a gap called The Noses near Schenectady, where I-90, railroad tracks, several local roads, the Erie Canal, the Barge Canal, and the Mohawk River all come together.
There’s a reason most roads use the route they do and why bicyclists tend to avoid any road named “Mountain”…
I believe many modern European freeways still roughly align to Roman roads and other trade routes that are centuries old. (And in any case if you check out a road map from the 1970s it’s still remarkably similar if you don’t pay too much attention to growing populations. Back in the 1950s there’s quite a bit more difference though.)
Around here, the “new roads” are inside housing developments; the main roads lie where they’ve always been: along the wagon tracks near the Hudson that connected village to village!
A lot of freeways were built roughly parallel to, but in different physical locations than the old roads, which have since become secondary roads. The secondary, older roads with roots going back many centuries also tend to be less straight. Most of these freeways were constructed after WW2, perhaps more specifically after 1950. By the 1970s construction of all the projects planned after the war had pretty much finished. The reason nothing much happened after that is perhaps primarily because new road building projects were subject to significantly stricter environmental regulations. Whatever the reason, the final 7km of the A4 (see the missing pieces on the map) has been under discussion since the late 1950s. In 2009 they finally started construction on some of the final stretches because they either took care of environmental concerns or found a legal loophole to ignore them or something.
Here in Antwerp they’re supposed to start on the final third of the ring road within a few years — also something that’s been coming for decades, but they’re still fighting about whether to build a bridge or a tunnel. Part of the concerns here is that we don’t want things to look too American — meaning building things without too much concern for the aesthetics, livability, and environment. Perhaps more specifically how expressways can be literal class-dividing walls, but also like how elevated roads and railroads can dominate the view in some American cities. Plus we also tend to make sure to plan space for cyclists.
Well, at least we don’t have to worry about that around here! [sigh]
Some years back, though, we rode an abandoned section of the Pennsylvania Turnpike: four lanes, 13 miles, and three tunnels. Even with absolutely no possibility of encountering a motor vehicle, it was very difficult to not watch for them…
That looks surprisingly good for something not used or maintained since the 1960s.
It wasn’t much worse than some roads that do get regular maintenance…
The layer of fog coming out of the tunnels was a surprise, though. The prevailing wind came from the other side, cooled below the dew point, and emerged as a flat cloud just about head-high.