Green’s Dictionary of Slang

1. (US Und.) highway robbery; as low toby, on foot, and high toby, mounted robbery.

1807		Sessions Papers Feb. 133/1: He..asked me if I had any objection of being in a good thing...I asked him when and [...] he replied it was low toby, meaning a fotpad [sic] robbery .
1812		Vaux Vocab. of the Flash Lang. in McLachlan (1964) 274: toby: to toby a man, is to rob him on the highway; a person convicted of this offence, is said to be done for a toby. The toby applies exclusively to robbing on horseback; the practice of footpad robbery being properly called the spice, though it is common to distinguish the former by the title of high-toby, and the latter of low-toby.
1822		Life and Trial of James Mackcoull 57: I have no doubt that Mackcoull tried his luck at low tobby [sic].
1949		Monteleone Criminal Sl. (rev. edn).

2. a robbery (other than on the highway).

1881

Newcastle Courant 25 Nov. 6/5: ‘It would be a grand game if it could be managed; but it can’t yer see, and cant’s a word wot blocks the toby.’ ‘Cant’s a word as has nothing to do with a good cracksman’.

3. (also tober) the road, the highway, esp. as a place where robbers and highwaymen can find their victims [no evidence yet exists, but it this ‘neutral’ use was the earliest sense].

1830		Lytton Paul Clifford III 113: You are a capital fellow [...] the bravest and truest gill that ever took to the toby.
1842		Edinburgh Rev. July 484: Cadgers on the fly are those who beg as they pass along the tober (road). Cadging on the fly is a profitable occupation in the vicinity of bathing-places and large towns.
1851		Lancaster Gaz. (Lancs) 24 May 2/5: Cadgers on the fly are those who beg of ladies and gentlemen as they pass along the ‘tober’ (road).
1859, 1860		Hotten Dict. of Modern Sl. etc.
1873		Sl. Dict. 324: Toby the road. The highwayman or swell robber was in old days said to be on the high toby, from the high or main road, while those meaner fellows, the footpad and the cutpurse, were but ‘low toby-men,’ from their frequenting the by-ways.
1895		Crowe Aus. Sl. Dict. 86: Toby, the highway.
1910		Derbys. Advertiser 2 Dec. 25/4: ‘For 40 years [...] I’ve padded the ’oof on the toby’.
1912		Leamington Spa Courier 20 Sept. 7/1: ‘Hoppy Bet isis one of the best all-round ‘gaggers’ [...] Bet has no equal on or off the ‘toe-be’ (road).
1933		M. Marshall Tramp-Royal on the Toby 5: The road is our mother most benign, and we are her sons who travel thereon: Sons of Toby. [Ibid.] 117: By the Toby you are to understand [...] At the base period of its coining it stood for stand and deliver, highwaymen, men with low ways.
1938		J. Curtis They Drive by Night 56–7: There was no sense in going on to the Great North Road. The coppers were hotter along that toby than anywhere else in England.

4. (also tobyman) a tramp; the life of tramping.

1931		E. Blair letter 4 Sept. in Complete Works X (1998) 228: As to new words, here are some [...] Toby, a = a tramp (Also ‘to toby’, etc.).
1933		‘George Orwell’ Down and Out in Complete Works I (1986) 176: These (omitting the ones that everyone knows) are some of the cant words now used in London: [...] A toby – a tramp.
1933		M. Marshall Tramp-Royal on the Toby 106: Two other Tobymen were also there.
1937		J. Worby Other Half 221: ‘That’s the best meal I’ve had since I came off the toby twelve years ago,’ he said. ‘You can’t beat cooking in a drum.’.

5. an area of responsibility, e.g. a police beat (equivalent to manor n.

1955

B. Hill Boss of Britain’s Underworld 56: And to add insult to injury [...] last night he left a stolen drag on my tobey.