Hippisley Cox reckons 'Harrow' is the 'Hoare' or 'Ancient' Way, which fits in with the derivation of hoar in this 'New' English Dictionary from 1932 (Odhams) - 'august...grey with age', etc. I think our old mate Alfred Watkins had something to say about hoarstones (ancient stones), but I couldn't find it in the index of 'The Old Straight Track', and the elderflower 'ale' is taking its toll.
As for the Pilgrims' Way to Canterbury which, as Chance says, goes over the Surrey Downs, Hilaire Belloc wrote 'The Old Road' about it.
Parallel routes - Portway, Harrow Way, etc. That seems to be a recurrent phenomenon worthy of exploration. In 'Prehistoric Ritual and Religion' (eds. Alex Gibson and Derek Simpson, 1998, Stroud: Sutton) there's Roy Loveday's essay, 'Double Entrance Henges - Routes to the Past?' (pp14-31), which notes the literal parallels between the orientation of henge entrances and 'Roman' and medieval trackways. I can't be arsed to retype it all word for word, but here's a taster...
'A herepath mentioned in an Anglo-Saxon charter...surviving as an alternative westerly route to that along the Kennet valley, runs from the Marlborough region across Overton Down to pass through the east and west entrances of Avebury... Durrington Walls...lies immediately adjacent to another medieval east-west route...Its popularity is demonstrated... by the deep hollow ways which mark its descent of Beacon Hill en route to Bulford ...A hint that the route was of some antiquity is furnished by its correspondence with the only substantial opening in the linear ditch system of the eastern Plain'
And...
'On Cranborne Chase...maps...reveal Knowlton/Brockington...as the node of the main pre-turnpike routes heading south to Poole and south-west to Dorchester - the former route still bisecting the great enclosure...aso, aso,'
And what of the 'disconcerting' phenomenon of the axes of Roman Roads parallelling the axes of henges, miles distant? This Loveday relates to the existence of 'braided' routes - ie, roads from A to B needn't follow a single line (ultimately established by turnpikes - now there's a philosophical question!)...'turnpike surveyors rationalised routes which had previously followed a number of different, parallel tracks, often as much as two miles apart'...
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