Etymology
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highway (n.)

Old English heahweg "main road from one town to another;" see high (adj.) in sense of "main" + way (n.).

High street (Old English heahstræte) was the word before 17c. applied to highways and main roads, whether in the country or town, especially one of the Roman roads. In more recent usage, it generally is the proper name of the street of a town which is built upon a highway and was the principal street of the place.

Highway robbery, robbery committed near a highway, is from 1707, formerly the only sort punishable in common law by death; as a trivial expression for something too costly, by 1886.

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highwayman (n.)
"one who travels the highways with intent to rob people" (often on horseback and thus contrasted to a footpad), 1640s, from highway + man (n.).
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pike (n.4)

"highway," 1812 shortening of turnpike.

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brigandage (n.)
"highway robbery by organized gangs," c. 1600, from French brigandage, from brigand (see brigand).
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expressway (n.)
by 1945, American English, from express (adj.) + way (n.). Express highway is recorded by 1938.
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motorway (n.)

"specialized highway for fast motor traffic," 1903, from motor- + way (n.). Earliest uses were hypothetical; the thing became a reality 1930s.

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clover-leaf (n.)

also cloverleaf, "the leaf of a clover plant," 1787, from clover + leaf (n.). Highway interchange sense attested by 1933, so called for the shape.

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off-ramp (n.)

"sloping one-way road leading off a main highway," 1954, from off- (adj.), from off (prep.), + ramp (n.).

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milepost (n.)

also mile-post, "post set up to mark the distance by miles along a highway, etc.," 1768, from mile + post (n.1).

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