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Highwaymen, by which i presume you are refering to the romantic figure of the 17th and 18th century mostly operated on reasonably well travelled roads. as road travel was still very unpopular, there may have been only a few carriages on a single road in any one night, and a single man, or in a pair could quickly nip away over the countryside before a carriage could alert any law enforces.

The road north from york to Newcastle was particularaly popular, as was the raod to the west coast from London. However there were also highwaymen operating in big parks in cities such as London heath.

A good book for more historaical information about highwaymen is "Dick Turpin: The myth of the English highwayman" by James Sharpe, but be prepared for any romantic notions to be shattered! hope this helps

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