Way is a very frequent word whose original meaning – path or road – survives mainly in compounds, e.g. highway, motorway, railway, runway, and in names of footpaths, e.g. the Pennine Way, and streets, e.g. Castle Way. It owes its frequency to the many fixed and semi-fixed phrases with meanings which developed from the original one, including direction or route (Are you sure this is the right way? / sideways / way out, or exit), distance in space or time (a long way, way back in the 1950s), method (a more economical way of heating your house), habits and customs (way of life) and aspects of something (better in some ways and worse in others).
We use by the way to introduce a topic which is metaphorically lying beside the path our conversation is travelling along, i.e. by the wayside. Either way, one way or another, no two ways about it and You can’t have it both ways share the concept of a fork in a road, where you have to choose one direction or the other. Similarly, anyway and always mean that you’ll get to the same place no matter which path you take. If you go out of your way to do something, you metaphorically take a longer route than your direct one, at the expense of extra time and effort.
Road and raid were originally the same word: Old English rād meant ‘riding’ or ‘an attack on horseback’. This second meaning is preserved metaphorically in the expression make inroads into/in/on something.
Finally, street is from strata, a short form of the Latin via strata, a road spread with paving stones. Related words, all containing the idea of material spread in a layer, include strewn (e.g. a desk strewn with books and papers), straw (once commonly used as a floor covering), stratum, stratified and stratosphere.
In many British housing estates, by the way, streets are named by re-using the same first element repeatedly, but with different second elements, e.g. Victoria Street, Victoria Avenue, Victoria Crescent, Victoria View, Victoria Way, Victoria Road. Names with Street have stress on the first element: Victoria Street, while the others are stressed on the second element: Victoria Avenue, Victoria Crescent, etc., though this principle can be overridden for contrastive purposes: “They said Victoria Street, not Victoria Road.”
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