Wellington, the capital city of New Zealand, has been called “Windy Wellington” and the “Windy City.”
   
“Notwithstanding so much is said about windy Wellington, yet the breeze of Wellington is preferable to the damp of Nelson” was printed in The Colonist on September 9, 1862. “Windy Wellington. — This description is fast becoming inapplicable” was printed in the Wellington Independent on December 20, 1862. “The soubriquet of ‘Windy Wellington’ has not been given to the port without reason” was printed in The Colonist on February 23, 1864. “‘Windy Wellington’ has become a proverb” was printed in The Evening Post on June 13, 1872.
   
“The windy city of Wellington” was printed in the New Zealander on April 15, 1857. “Talking of Wellington, I must congratulate that windy city” was printed in the Otago Witness on September 10, 1870. “Windy City” was printed in the Saturday Advertiser on November 17, 1877. “Of course this is a very laudable view as far as Wellington is concerned, but fortunately there are other places than that Windy City to be considered” was printed in the Ashburton Garden on December 23, 1882. “Breezes from the Windy City” was printed in the Wairarapa Daily Times on August 4, 1888.
     
Other cities with a “Windy City” nickname include Chicago, Illinois and Port Elizabeth, South Africa.
 
 
Wikipedia: Wellington
Wellington (Māori: Te Whanganui-a-Tara [tɛ ˈfaŋanʉi a taɾa]) is the capital city of New Zealand. It is located at the south-western tip of the North Island, between Cook Strait and the Remutaka Range. Wellington is the major population centre of the southern North Island, and is the administrative centre of the Wellington Region, which also includes the Kapiti Coast and the Wairarapa. It is the world’s southernmost capital of a sovereign state. Wellington features a temperate maritime climate, and is the world’s windiest city by average wind speed.
   
Papers Past 
PROGRESS OF THE WELLLINGTON REVOLUTION.
NEW ZEALANDER, VOLUME 13, ISSUE 1147, 15 APRIL 1857, PAGE 2
(...)
And, on the other hand, there is much more than at first sight meet; the eye in the remark about the jealousies saw dissensions that would be the inevitable result of the General and Provincial Government: being,’ brought into such close contact in the windy city of Wellington.
     
Papers Past
NELSON AND WELLINGTON.
COLONIST, VOLUME V, ISSUE 509, 9 SEPTEMBER 1862, PAGE 1
(...)
In our humble opinion Nelson must yield the palm to Wellington as a healthy situation. Notwithstanding so much is said about windy Wellington, yet the breeze of Wellington is preferable to the damp of Nelson.
     
Papers Past
Local Intelligence.
WELLINGTON INDEPENDENT, VOLUME XVII, ISSUE 1806, 20 DECEMBER 1862, PAGE 3
(...)
Windy Wellington. — This description is fast becoming inapplicable. Very recently the Wesleyan Church at Otago, was seriously injured by the wind, and on the Lachlan in Australia, we read that during a recent terrible thunderstorm, the Wesleyan and Catholic Churches were blown down.
     
Papers Past
THE COLONIST.
COLONIST, VOLUME VII, ISSUE 660, 23 FEBRUARY 1864, PAGE 2
(...)
Wellington harbor for extent is admittedly one of the finest in New Zealand; but the soubriquet of “Windy Wellington” has not been given to the port without reason. The spacious harbor is so subject to frequent and violent gales from the north-east and southwest, that steamers frequently are obliged to have both anchors down, and in addition to keep full steam on to prevent them dragging. Pull-rigged ships have been blown from their anchorage in the middle of the bayharbor, and driven ashore.
   
Papers Past
Untitled
OTAGO WITNESS, ISSUE 980, 10 SEPTEMBER 1870, PAGE 13
(...)
Talking of Wellington, I must congratulate that windy city on having about the tallest talker, or rather writer, I have met with for a long time.
 
Papers Past
The Evening Post. THURSDAY, JUNE 13, 1872.
EVENING POST, VOLUME VIII, ISSUE 112, 13 JUNE 1872, PAGE 2
(...)
“Windy Wellington” has become a proverb, but the meteorological observations published in yesterday’s Gazette, prove that Wellington is not par excellence the windy city of the colony ; in fact Auckland and Napier surpass it. while Wanganui, Southland, and Dunedin nearly come np to it for wind. According to the return before us, the average daily force in miles for the month of April in Wellington was 202, but in Auckland, for the same time, it was 264, and in Napier 210. What will our Auckland friends say now about “windy Wellington.”
   
Papers Past
Untitled
WELLINGTON INDEPENDENT, VOLUME XXIX, ISSUE 4053, 14 MARCH 1874, PAGE 2
(...)
Wellington has the reputation, and perhaps it is not undeserved, of being a somewhat windy city. From that point of view yesterday was a rather remarkable day, not a breath of wind having prevailed, beyond very light cats’ paws, from morning to night.
   
Papers Past
THE Daily Southern Cross.
DAILY SOUTHERN CROSS, VOLUME XXXI, ISSUE 5437, 18 FEBRUARY 1875, PAGE 4
(...)
Oh, windy city of the South, may airs from Heaven teach your rulers, if not generosity, at least justice!
   
Papers Past
THEATRICAL ITEMS.
SATURDAY ADVERTISER, VOLUME III, ISSUE 123, 17 NOVEMBER 1877, PAGE 9
(...)
Wellington has been flooded with amusements during the past week or two. The Theatre Boyal, the Princess Theatre, St. George’s, and the Oddfellows’ Hall have had each a company “holding the mirror up” to the public of the Windy City.
 
Papers Past
The Ashburton Guardian. Magna Est Veritas et Prevalebit. SATURDAY, DECEMBER 23, 1882. An Odious Comparison.
ASHBURTON GUARDIAN, VOLUME IV, ISSUE 826, 23 DECEMBER 1882, PAGE 2
(...)
Of course this is a very laudable view as far as Wellington is concerned, but fortunately there are other places than that Windy City to be considered, and which have equally strong claims in affording a suitable site for the seat of Government
     
Google Books
Random Rot:
A Journal of Three Years’ Wanderings about the World
By James Edge-Partington
Altrincham, UK: Printed at The Guardian Office
1883
Pg. 242:
Windy Wellington, as it is called, deserves its name, for it can blow here, of which we have had some experience. Not only dust, but pebbles, are lifted up by the force of the wind.
 
Papers Past
DOWN SOUTH BY THE EAST COAST. THE EMPIRE CITY.
OBSERVER, VOLUME 7, ISSUE 353, 12 SEPTEMBER 1885, PAGE 23
(...)
Wellington says she shall not have the little truck, and is very jealous of her Southern neighbors endeavour to collect so much money out of the public purse. In fact there s the devil to pay in the windy .city, and the papers are kept full just now all over the colony with little else but Parliamentary matters on this .all-important question.
   
Papers Past
NEW YEAR’S DAY.
NEW ZEALAND TIMES, VOLUME XLVIII, ISSUE 7972, 1 JANUARY 1887, PAGE 2
NEW YEAR’S DAY.
To-day, being New Year’s Day, will be a holiday, and a day of holiday-making. The weather so far for the holidays has been glorious, and if it is fine to-day Wellington will have for ever freed itself from reproach as “a windy city.”
   
Papers Past
NAPIER NONSENSE
OBSERVER, VOLUME 8, ISSUE 435, 23 APRIL 1887, PAGE 18
(...)
The Wellington cricketers came up and teased the life out of our local men, and showed them how they play cricket in the windy city
   
Papers Past
Breezes from the Windy City.
WAIRARAPA DAILY TIMES, VOLUME IX, ISSUE 2968, 4 AUGUST 1888, PAGE 2
Breezes from the Windy City.
(By Boreas).. Depression! depression! This is all the cry in Wellington just now.
     
Papers Past
FOOTBALL.
AUCKLAND STAR, VOLUME XXXII, ISSUE 147, 22 JUNE 1901, PAGE 4 (SUPPLEMENT)
(...)
Mr. F. J. Ohlson left for Wellington last week to attend the conference of referees at that centre. While in the Windy City he intends, of course, to have.a look at Wellington football, and should be able to give us on returning the “strength” of the probable Wellington rep. team, of which I hear great accounts.
 
Papers Past   
BOXING MATTERS
EVENING POST, VOLUME CIX, ISSUE 36, 12 FEBRUARY 1925, PAGE 9
Sir,—Last evening I attended the boxing contest m the Town Hall, and, like a good many others, .purchased a programme for the sum of sixpence. It was with great regret that I noticed in a paragraph introducing the professional contestants the. committee saw fit to make the statement that this was the first appearance of the boxers in the ‘windy city.” In latter years. Wellington has not suffered from wind any more than any other city,: and even if so, it is ill-advised, belittling, and cheap for a Wellington body to refer to the city as “the windy city.”
 
OCLC WorldCat record
Windy city ; Ain’t it a shame
Author: Pixie Williams; Ruru Karaitiana; Ruru Karaitiana Quintette,
Publisher: [Wellington] : Tanza, [1949]
Edition/Format:   Music : 78 rpm : English
 
Papers Past
DAYZ IN LIFE OF NZ ROCK BAND PART 1 ROUGH JUSTICE
RIP IT UP, ISSUE 22, 1 MAY 1979, PAGE 1
Then it’s back to the Windy City.
 
Papers Past
Rumours
RIP IT UP, ISSUE 25, 1 AUGUST 1979, PAGE 6
WELLINGTON
(...)
... the Windy City Strugglers, ...
 
OCLC WorldCat record
The Windy City Strugglers.
Author: Windy City Strugglers (Musical group)
Publisher: Wellington, N.Z. : Eelman Records, ℗1994.
Edition/Format:   Music CD : CD audio : English
   
Google Books
The New Partridge Dictionary of Slang and Unconventional English: J-Z
By Tom Dalwell and Terry Victor
New York, NY: Routledge
2006
Pg. 2110:
Windy City nickname
1. Chicago, Illinois US 1976
(...)
2. Port Elizabeth SOUTH AFRICA 1989
(...)
3. Wellington, New Zealand NEW ZEALAND
(A 2004 citation is given.—ed.)
 
NickBallesteros.com
11 January 2009
Wellington, the windy city!
Wellington is also known as the windy city, or the city of sails. It’s because the westerly wind drifts of over 60km per hour rushes through the city at least five times more frequently than in any other city in New Zealand.
Posted by Nick Ballesteros at 5:38 pm