Spotted gliding across the streets of Chicago in a zig-zag pattern are long wooden boards – two monstrous large wheels and riders in their early 20’s – whizzed past the pedestrian crosswalk. This is nothing unusual — longboarders are not new to the Windy City, but another group of these riders might surprise you.

Most Chicagoans have grown accustomed to the occasional flashed blur of wooden boards, the loud rattle of hard wheels colliding with the rough city streets, and avoiding near-on-collisions with those trying to cross the busy roads on these rolling decks.

Is this something that will eventually fade?

Trends have been noted of longboards within the past couple of years in Chicago, but it’s mainly associated with college-aged students. These demographics would suggest that longboarding is timely, and therefore it may be considered a fad since you eventually graduate college and grow out of it. The issue with this is that longboarding also reaches an older demographic.

According to Chicago’s Windward Boardshop owner, Jess Bell, the main demographics of riders in Chicago fit two main criteria. There are the typical college students that come into the store to buy longboards as a means of commuting and transportation around campus. Then there are the retiree skateboarders in their mid 20’s-30’s who would like to regain the thrill of skateboarding, without being associated with adolescents and childish behavior.

Bell is not alone; skateboard shops across Chicago noted the new clientele purchasing these boards.

Citizen Skate Cafe, located in Wilson Avenue in Chicago, is a skateboard shop that sells both coffee and skateboards. Hannah Weimer, employee at the shop, noticed similar demographics.

“Most of the clients we get here purchasing longboards are the older generations, around 30 and older,” said Weimer. “There has definitely been an increase in the sales recently, and more people are requesting longboards than before. It gives people a peace of mind that they can still do what they like and not be judged for it or have anyone think they’re too old to longboard.”

The history of longboarding dates back to the late 1950’s in Hawaii, where surfers developed this activity to cruise when the waves were dull. Over time this activity advanced into a sport and began trending in areas of the West Coast of the U.S. – specifically in California. Although this sport started off as an alternative to surfing in Hawaii, and then California, it has made its way over to Chicago as a means of transportation and reliving a past hobby without negative connotations.

Longboarding in Chicago is continuing to increase in popularity. With cold weather approaching, skateboarders and longboarders alike are trying to take advantage of the streets before they get icy.

A Facebook group dedicated to longboarders in the Chicago area called the “Chicago Longboarding Society,” has reached a membership of 1,489 people. This group on Facebook originated to help local Chicagoans meet and have longboard sessions together. Eventually this group transitioned into a place to post longboarding videos, general discussions about longboarding, and even as a place to sell longboards and skateboard equipment to local Chicagoans.

The Chicago Longboard Society recently held a longboarding Halloween event in Humbolt Park, Oct. 30. The race, called the “Big Scary Push,” was an 8.8-mile longboarding costume party where longboarders dressed up in Halloween costumes and raced on their boards. Some costumes ranged from Superman, a yellow chicken suit, to a maid with a vacuum – all racing on longboards.

The Chicago Longboard Society has even scheduled an upcoming event for Thanksgiving to get in a skate session before the snow and to catch up with those who had been busy with school.

Despite skepticism and approaching cold weather, this sport doesn’t seem to be permanently fading anytime soon.