Green’s Dictionary of Slang

milestone n.

a country bumpkin.

1812		Vaux Vocab. of the Flash Lang.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.

SE in slang uses

In compounds

milestone inspector (n.)

(UK tramp) a professional tramp.

1898		Northampton Mercury 8 Apr. 3/3: John Cope [...] a milestone inspector, was admitted to the casual ward of the Kettering workhouse.
1904		Western Times 16 Aug. 8/2: A ‘Mile Stone Inspector’ Makes Bother at Cullompton [...] Thomas Mills, a ‘milkestone inspector,’ was charged [...] yesterday with being drunk and disorderly.
1912		Derby Dly Teleg. 19 Nov. 3/3: A homeless and unknown labourer [...] was charged with being drunk and disorderly [...] when asked what his trade was prisoner replied that he was a milestone inspector.
1925		Exeter & Plymouth Gaz. 5 June 11/5: Workhouse Masters wityh any experience at all will soon detect the regular ‘mile-stone inspector’.
1932		F. Jennings Tramping with Tramps 211: Milestone Inspector – a professional tramp.
1959		I. & P. Opie Lore and Lang. of Schoolchildren (1977) 175: A tramp, very generally, is a ‘milestone inspector’.

milestone-monger (n.)

(tramp) a professional tramp.

1883		J. Greenwood Tag, Rag & Co. n.p.: Of all men I should be the last to utter a harsh word against the most inveterate milestonemonger that ever fled from his family to enjoy the sweets of freedom. J.
1890–1904		Farmer & Henley Sl. and Its Analogues.