A “Hoboken Special” is old restaurant slang for an order of pineapple soda and chocolate ice cream. Columbia University’s Harold W. Bentley first recorded the term in “Linguistic Concoctions of the Soda Jerker,” published in American Speech in February 1936.
 
Hoboken, in the 1920s and 1930s, was blue collar town known for its jobs in the Port of New York and New Jersey. “Pineapple” was 1930s slang for a hand grenade, and this often was reflected in soda jerk slang of “Chicago” (home of gangsters such as Al Capone) for “pineapple soda.” Legends (or facts) of Hoboken’s tough longshoremen using “pineapples” (hand grenades) probably is the reason for the name “Hoboken Special.” The term is of historical interest today.
 
   
Wikipedia: Hoboken, New Jersey
Hoboken (/ˈhoʊboʊkən/ ho-bo-ken; Unami: Hupokàn) is a city in Hudson County, New Jersey, United States. As of the 2010 United States Census, the city’s population was 50,005,having grown by 11,428 (+29.6%) from 38,577 counted in the 2000 Census, which had in turn increased by 5,180 (+15.5%) from the 33,397 in the 1990 Census. Hoboken is part of the New York City metro area and contains Hoboken Terminal, a major transportation hub for the region. Hoboken is also the location of the first recorded game of baseball (although this is disputed) and of the Stevens Institute of Technology, one of the oldest technological universities in the United States.
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Its waterfront was an integral part of the Port of New York and New Jersey and home to major industries for most of the 20th century. The character of the city has changed from a blue collar town to one of upscale shops and condominiums. Hoboken is part of the New Jersey Gold Coast.
 
Hobokeni.com
Luckily, I live in Hoboken where my need for a cool, smooth “homemade” treat can be satiated. After all, this town has an ice cream soda named after it: the “Hoboken special” made with pineapple soda and chocolate ice cream. As legend has it, the Hoboken special comes from the city’s raging longshoremen’s use of a “pineapple” hand grenade to intimidate.
 
JSTOR
February 1936, American Speech, “Linguistic Concoctions of the Soda Jerker” by Harold W. Bentley, pp. 37-45:
HOBOKEN SPECIAL: Pineapple soda with chocolate cream.
   
10 June 1951, Miami (FL) Sunday News, “A Language Of Their Own” by Harvey Keeler, Miami Sunday News Magazine sec., pg. 5, col. 1:
A “Hoboken” is a pineapple soda with chocolate ice cream and a nana split.
 
March 1960, Fast Food, “Fountain Service” by Harry Press, pg. 40, col. 1:
I entered pharmacy about 39 years ago.  The first store I worked in had a soda fountain, and I fell in love with that end of the business.
 
In those days, soda fountain workers had a language all their own.  In order to save (Col. 2—ed.) time, or just to be different, they used abbreviations or code words, or numbers for almost everything they ordered.
   
Some of these were quite clever, but some were often embarrassing to the customers.  For this reason, most chain (Col. 3—ed.) stores and a great many independents have stopped using them.
   
Here are a few of the “codes” still used behind some fountains.
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Hoboken—pineapple soda, chocolate ice cream.
 
Google Books
Hash House Lingo:
The Slang of Soda Jerks, Short-Order Cooks, Bartenders, Waitresses, Carhops and Other Denizens of Yesterday’s Roadside
By Jack Smiley
Mineola, NY: Dover Publications, Inc.
2012 (Originally published in 1941)
Pg. 62:
Hoboken special—pineapple soda with chocolate ice cream.