Boystown flies the W as Chicago Cubs return for World Series

Fri. October 28, 2016 11:23 AM by News Staff

chicago cubs host cleveland indians at wrigley field

photo credit // anthony meade

Wrigleyville and Boystown neighborhoods remain busy destination all weekend

Chicago, IL - Halloween weekend in Chicago's Boystown neighborhood is usually packed with drag queens, Speedo-clad gentlemen and costumes paying homage to pop culture, but this year, you'll also see it turning Cubbie Blue.

As the Chicago Cubs host the Cleveland Indians this weekend for Games 3, 4 and 5 (if necessary) of the World Series, many of the gayborhood's most popular bars and nightclubs are showing serious support for their closest neighbors.

Wrigley Field – the Cubs' 102-year-old ball park – and Wrigleyville are practically within spitting distance of Boystown, the city's LGBT neighborhood. While the two neighborhoods may seem radically different, LGBT sports historian Bill Gubrud told that the Chicago Cubs and their fans have always been good neighbors.

"Wrigley is an amazing place to watch a game and it remains the most welcoming ballpark to the LGBT community anywhere in the country," said Gubrud, who is executive director of the National Gay & Lesbian Sports Hall of Fame (NGLSHF).

In fact, the Cubs have hosted a "gay day" at the ballpark every year since 2001. Out at Wrigley is the longest-running LGBT-themed day among the 30 Major League Baseball teams, with the Cleveland Indians hosting only one LGBT-themed event at their stadium, according to OutSports.

That's on top of the Chicago Cubs becoming the first MLB team to have an openly gay owner in 2009 when the Ricketts family took over ownership of the Cubs from the Tribune Company. Laura Ricketts, a prominent lesbian, is part of the active family management.

Under the Ricketts family, the Cubs made the bold decision to enlist "Mr. Cub" Ernie Banks to represent the team at the annual Chicago Pride Parade in 2010. The team has participated in the parade each year since with Cubs player and Hall of Famer Ryne Sandberg riding the team float this past summer.

Plus, in 2011, the Cubs became one of the first MLB teams to release a pro-gay "It Gets Better" video, which featured Cubs pitcher Ryan Dempster and Darwin Barney.

The Chicago Cubs' rich history with the LGBT community earned them a place in the Chicago-based NGLSHF during a 2013 ceremony at Center on Halsted. It's also why so many Boystown mainstays are hosting Cubs-themed events this weekend.

"Sidetrack is thrilled for the Cubs being in the World Series," said Sidetrack GM Brad Balof. "Lakeview, Wrigleyville and Boystown are great entertainment districts that are prepared to welcome the large crowds with open arms."

With no cover, a giant HD screen, and seven bars to watch the games, Sidetrack, 3349 N. Halsted, will undoubtedly be packed this Halloween weekend.

Across the street from Sidetrack sits the fully decked-out Roscoe's Tavern, 3356 N. Halsted, its windows decorated in Cubbie Blue and W signs in hopes the team brings home the win. (The Cubs last won in 1908.)

The entire weekend is sure to be fun – and packed. Ald. Tom Tunney's (44th Ward) office already announced strict parking restrictions, and WBEZ Chicago did a full feature on the upcoming weekend and potential security issues.

"Halloween is a huge gay holiday," popular drag queen Trannika Rex told WBEZ. "So all of the gays are going to be out, and then all of the straight people are going to be out, and you worry about having two hordes of people directly next to each other at their supreme drunkest."

Bar owners in Boystown, however, are confident the weekend will go smoothly.

"We are prepared for large crowds," added Sidetrack's Balof. "Police have advised patrons to save time by not traveling with bags or large purses and to prepare for lines and additional travel time."

For more information on the happenings this weekend, check out the calendar to view all the most popular events.

Related: Neighborhood parking restrictions, checkpoints for World Series this weekend