Walking through the leaf-laden streets of the city, one will notice that almost every bar has decorated its interior and/or exterior with Halloween paraphernalia. Skeletons, cobwebs, pumpkins and drink specials galore help Chicagoans celebrate the one day when people can act and look ridiculous and be perfectly socially acceptable. But deep in the heart of the city is a neighborhood that takes the haunted holiday to an entirely

new dimension.

Boystown has long been known for throwing a Halloween spectacular unlike any other. For years, people from all across the Chicagoland area and the state take part in a weekend celebration that continues, even after bars close. This year, with Oct. 31 falling on a Monday, bar owners and residents anticipate a long weekend of costume contests and drag competitions ending with the parade, expected to draw the largest crowd ever.

“I think Boystown represents Chicago as the Halloween spot,” said Shawn Hazen, promotions and marketing manager of Boystown bar Roscoe’s, 3356 N. Halsted St. “[The holiday] in other neighborhoods and other spots of the city is just [another weekend], it’s a reason for people to get drunk. Boystown does it as an event, from the parade to the costume contests; it’s an all-consuming amazingness.”

One of the aspects that draws large crowds to Boystown is the great number and variety of events that most bars offer. Sometimes starting a week before Halloween, people are invited to enjoy extravagantly themed parties, drag queen competitions and wet-boxer contests by the plenty.

The bar Sidetrack, 3349 N. Halsted St., hosts its annual “Night of 100 Drag Queens,” a fundraiser that benefits Equality Illinois and features performances from both amateur and professional drag queens. Chuck Hyde, co-owner and general manager of Sidetrack, said the bar only does drag once a year and for that reason a lot of thought, time and energy go into making it a spectacular show.

“Between the performers, staff and audience, you’ll see [more than] a hundred drag queens, some more classic and others more inventive and crazy,” Hyde said. “It’s always a great experience.”

Along with drag queens, Boystown residents are best known for putting together the most unique and outlandish costumes in the city. From topical news references like last year’s trapped coal miners, to dragons and every take on every celebrity you can think of will be featured on Halsted Street. Sean Kotwa, director of operations at Hydrate, 3458 N. Halsted St., said the Boystown community has a lot of members who are designers or come from a creative background, so a lot of attention is paid to the costumes. He added that the gay community also loves the art of impersonation, so a lot of very realistic and over-the-top pop figures will be seen.

“Boystown is the place people want to show off their costumes and so if you really want to see the hottest costumes in town, you’re going to see them on Halsted,” Hyde said.

And Boystown isn’t only a Halloween hot spot for the gay community. Hyde said thousands of people, gay and straight, come from different parts of the city to partake in the events and costume competitions the area offers. The entire event has grown as the community has grown, he said. Back when the area only had a handful of bars, the parade and the weekend festivities weren’t as extravagant as they are now. But as the number of businesses and people who live in the community have increased, the insanity of the Halloween weekend has too.

The parade is perhaps the part of the holiday weekend that has grown the most. In its 15th year, the parade has expanded from a small sidewalk gathering to a 0.7 mile trek complete with floats and fire-breathing cars. According to Kotwa, who is also a chair of the parade, 50,000–65,000 people are anticipated to be involved. Hyde agreed that in his 30 years at Sidetrack, he has seen the community really help create something special with the parade.

Sandra Klein, a board member with Triangle Neighbors Association, said the parade, which the group initially started, became too big for the small community organization to handle, so TNA gave it to its current sponsor, the NortHalested Business Alliance. The event first began with a few people parading in the streets before going to the bars, and has turned into a fundraiser, aiding in accumulating enough money to build Space Park, 815 W. Roscoe St., which it did a few years ago.

One change to this year is separating the children’s part of the parade and putting it on Sunday rather than Monday. The route has also been extended a little further to accommodate the size of the parade. After the parade finishes, there is live music as well as theatrics from “Musical of the Living Dead” and other performers. Hyde said he is happy because Boystown finally got its night parade, since the Pride Parade and Market Days are daytime.

But the action isn’t done after the parade. Hyde said the bars still do events like costume contests throughout the night. Kotwa agreed that having Halloween fall on a Monday is best because it gives them Friday through Monday to “play around with all the costumes.”

“In general, I think it’s the craziest Halloween you’ll find,” Hazen said. “I think Boystown covers the holiday for the entire city. [The neighborhood] sums up everything that is Halloween in Chicago, from the parade to the costume contests. And with Halloween falling on a Monday, there will be an entire weekend of madness and debauchery.”