For the longest time, the soundest explanation on the origins of the term "habitants" was a tale involving New York Rangers owner Tex Rickard sometime in the late 1920's. As that version went, Rickard, a promoter known North America wide, had spoken the phrase in the New York media, and it spread from there. By all acounts, that is likely the origin of how Americans came upon the term, but it is not the true origin of the term itself in how it concerned the Canadiens.
Rickard explained back in the day, that the word "habitant'' had rural connotations, and he invoked the farming populace of the province of Quebec in suggesting that a great many of the Canadiens players came from the habitants of the vast land. Rightfully or not, Rickard is often credited with being of the first to shorten the term to "Habs", and since he was quite the quote back then, spread the term far and wide.
As with many of the Montreal Canadiens myths and legends, the truth and fact behind them is much simpler. The noun "habit" in french or english, is defined as "the bodily appearance or makeup especially as indicative of one's capacities and conditions".
Continuing in that line of thinking, is exactly what Canadiens fans in February 1914 likely had in mind, as they decided to dress distinctively to cheer on their local favorites for games at the Westmount Arena. The distinctive dress code was neccessary at that time, as the Canadiens were not the lone tenants at the arena. The Westmount in fact, had two local clubs - the Canadiens and the Montreal Wanderers.
Supporters of the Canadiens sought to sort themselves from those of their rivals, and took steps in that direction by donning everything head to toe from woolen toques, multicolored belts to pearl embroidered mocassins. The "habitants" look caught on, and soon the term itself spilled over into the Montreal sports pages.
In a February 9, 1914 edition of Le Devoir it was remarked that "les Habitants" continuously dominated the Wanderers on the evening.
"Le Canadien a administré la défaite la plus complète aux équipiers du Toronto samedi soir, devant une assistance monstre comme seuls nos équipiers savent en amener à l’Arena, résultat final 9 à 3. Sans contredit les " Habitants " eurent l’avantage continuellement… ".
In the same paper one week later, the term had moved up to the subtitle that read ''les Habitants blaked the Senators after 6 minutes of overtime.''
"PARTIE SENSATIONNELLE À MONTREAL SAMEDI. Les "Habitants" blanchissent l'équipe des Sénateurs après six minutes de jeu supplémentaire."
The photo included in this post from Le Devoir and some of the content of this article were translated from Paul Foisy's site Sport et Societe Quebec. Mr Foisy's article ends on a suggestive note, saying that for all years the Canadiens fans have been chanting "Go Habs Go!", it's unfortunate they do not still dress for the role as their hockey ancestors had.
I don't know about that!