Green’s Dictionary of Slang

1. any quiet provincial place.

1856		Hull Packet 5 Sept. 4/5: A ‘tranquil spot’ [...] We have long regarded Hedon as the ‘Sleepy Hollow’ of Holderness.
1877		S. James Vagabond Papers (4th series) 189: Sydney has had the reputation of being a regular Sleepy Hollow compared to the Victorian capital.
1880		Bulletin (Sydney) 9 Oct. 8/2: Uncle Tom and the Octaroon, with darkie business, are played out, even in Sleepy Hollow.
1883		Bury & Norwich Post 25 Dec. 6/2: This sequestered glen has long been known by the name of ‘Sleepy Hollow’.
1887		Bulletin (Sydney) 15 Oct. 9/1: In the old days, [...] the ‘sports’ of that one-horse, sleepy hollow got up a race meeting.
1934		Townsville Daily Bulletin (Qld) 1 Mar. 10/4: Hittin’ Bowen [...] I wasted no time in samplin’ the brew of ‘Sleepy Hollow’.
1963		Arlington Heights Herald (IL) 5 Sept. 10/1: Driving through picturesque Sleep Hollow, the visitor [...] notes the sceneic streams, lakes and wooded areas.
1985		McGill G’day Country 77: Through the [Rimutaka] tunnel are the country’s mostregularrun of sleepy hollows, from Featherston through Greytown and Carterton.
1997		A. Highcrest At Home on the Stroll 222: This illustrates just how far some people are willing to go to create their own versions of Sleepy Hollow.
2006		L.A. Times 16 Apr. 159/1: Sleepy Hollow is an escape from life’s bustle [...] is all about seclusion, nature and the longevity of tradition.

2. (N.Z.) Nelson, New Zealand; also attrib.

1857		Nelson Examiner 2 May 2: Nelson appears to have become a second ‘sleepy hollow’, and unless we rouse ourselves speedily we shall be known [...] as ‘sleepy-hollow boys’ [DNZE].
1877		Country Journal I 251: The ‘Sleepy Hollow’ boys [i.e. the Nelson football team] rode rough shod over boisterous Wellington [DNZE].
1887		Auckland Weekly News 24 Sept. 28: Our visit ended at Nelson—generally spoken of as ‘Sleepy Hollow’ [DNZE].
1891		in M. Wilson Land of the Tui (1894) 218: In summer, when the heat is semi-tropical, I am told that Nelson fully merits its soporific title of ‘Sleepy Hollow’ [DNZE].
1910		Fanning Players and Slayers 87: In his time B. Fanning was in some fierce battles, and the roughest of them was at Nelson, misnamed ‘Sleepy Hollow’ [DNZE].
1937		N.Z. Railways Mag. Oct. 23: In spite of the fact that Nelson is called ‘Sleepy Hollow’ it seems to me always that it is Marlborough that is the quiet province [DNZE].
1956		Sutherland Green Kiwi (1960) 172: While we were driving along...Nelson harbour...Glennie remarked: ‘They call this place “Sleepy Hollow”, you know. I’ve heard it said that you’ll sleep a couple of hours longer here than you will anywhere else—it’s something to do with the air, they say.’ [DNZE].

3. (US Und.) Trenton Prison, New Jersey.

1949

Monteleone Criminal Sl. (rev. edn).

4. (S.Afr.) Pietermaritzburg.

1949		O. Walker Proud Zulu (1951) 139: Never had such an array of V.C.’s, CB.’s, and titles descended in scarlet and gold upon ‘Sleepy Hollow’ as the little rustic, Dutch-gabled capital of Maritzburg was known [DSAE].
1988		Frontline Mar. 11: Blood River at Sleepy Hollow. No one has ever been interested in Maritzburg. People have called us ‘Sleepy Hollow’. Now we are suddenly in the spotlight [DSAE].
1994		Natal on Sat. 8 Jan. 11: Party-time in the Sleepy Hollow. It’s party time in Pietermaritzburg, and the Natal capital seems hell-bent on shrugging off its ‘Sleepy Hollow’ tag [...] Cynics had better note — ‘Sleepy Hollow’ is wide awake [DSAE].