Flickr/Estelle Spencer

Date

Event

Location

Sep 23 Wed

Track down a good pumpkin beer Pumpkin beer is another one of those things that pops up around this time, and, like haunted houses, most of them suck. While Pumking is a favorite in many beer circles and Good Gourd is the number one pumpkin beer according to, you know, us, the best might be Elysian Punkuccino, made with pumpkin flesh and Stumptown coffee (it’s better than it sounds). Or just stick with an appropriately fallish beer like Lagunitas Little Sumpin’ Extra. Close enough.

Liquor stores around Chicagoland

Track down a good pumpkin beer Liquor stores around Chicagoland Pumpkin beer is another one of those things that pops up around this time, and, like haunted houses, most of them suck. While Pumking is a favorite in many beer circles and Good Gourd is the number one pumpkin beer according to, you know, us, the best might be Elysian Punkuccino, made with pumpkin flesh and Stumptown coffee (it’s better than it sounds). Or just stick with an appropriately fallish beer like Lagunitas Little Sumpin’ Extra. Close enough.

Flickr/Leigh Wolf

Date

Event

Location

Sep 23-Oct 4

Squeeze in one more booze cruise Who says you need to dock that boat for the season after Labor Day? Certainly not your buddy the boat owner (or so you tell him) or several of Chicago’s finest booze cruise emporiums, many of which offer fall events like beer tastings and flights through late September.

Multiple locations

Squeeze in one more booze cruise Multiple locations Who says you need to dock that boat for the season after Labor Day? Certainly not your buddy the boat owner (or so you tell him) or several of Chicago’s finest booze cruise emporiums, many of which offer fall events like beer tastings and flights through late September.

Date

Event

Location

Sep 23-Oct 31

Hit as many Oktoberfests as you can handle In case you didn’t get it by now, Chicagoans like their beer. So much so that every fall, the city gives birth to more Oktoberfests than even a seasoned pro like Clark Griswold can get chased from in one sitting. Thankfully, every year we compile a list of all the Oktoberfests worth going to, which you would wise to consult before strapping on the lederhosen.

Multiple venues

Hit as many Oktoberfests as you can handle Multiple venues In case you didn’t get it by now, Chicagoans like their beer. So much so that every fall, the city gives birth to more Oktoberfests than even a seasoned pro like Clark Griswold can get chased from in one sitting. Thankfully, every year we compile a list of all the Oktoberfests worth going to, which you would wise to consult before strapping on the lederhosen.

Flickr/vxla

Date

Event

Location

Sep 23-Dec 20

With festival season over, turn to local clubs for live music  Summer is great for festivals and all, but fall is easily the number one season for concerts at local clubs as bands tour on new releases. Check out acts like Gang of Four at Thalia Hall, Yo La Tengo at the Vic, and Chvrches at Metro, or just wander into a place like Green Mill or Empty Bottle and let the venue do the rest.

Multiple venues

With festival season over, turn to local clubs for live music  Multiple venues Summer is great for festivals and all, but fall is easily the number one season for concerts at local clubs as bands tour on new releases. Check out acts like Gang of Four at Thalia Hall, Yo La Tengo at the Vic, and Chvrches at Metro, or just wander into a place like Green Mill or Empty Bottle and let the venue do the rest.

Date

Event

Location

TBA

Sample all the amazing brews at Beer Hoptacular The crunch of leaves beneath your feet can only mean one thing: Beer Hoptacular is right around the corner. The annual fall rite of passage is always a highlight of the season, although this year they are really driving the suspense as they have still not announced when or where the hell it’s taking place… other than “Fall 2015.”

Venue TBD

Sample all the amazing brews at Beer Hoptacular Venue TBD The crunch of leaves beneath your feet can only mean one thing: Beer Hoptacular is right around the corner. The annual fall rite of passage is always a highlight of the season, although this year they are really driving the suspense as they have still not announced when or where the hell it’s taking place… other than “Fall 2015.”

Date

Event

Location

Oct 1-Nov 1

Go to an actually semi-decent haunted house This time of year is famous for pop-up “haunted houses” in malls that are about as scary as spending an afternoon in Abercrombie. Instead, check out an actually good haunted house like Statesville Haunted Prison, winner of numerous accolades and consistent provider of “worth it” haunted house nightmares.

Crest Hill, Illinois

Go to an actually semi-decent haunted house Crest Hill, Illinois This time of year is famous for pop-up “haunted houses” in malls that are about as scary as spending an afternoon in Abercrombie. Instead, check out an actually good haunted house like Statesville Haunted Prison, winner of numerous accolades and consistent provider of “worth it” haunted house nightmares.

Flickr/Stephen M. Scott

Date

Event

Location

Oct 4 Sun

Hit a Bears game, obviously Despite the low expectations of success on the field this year, nothing can take away from the ambiance that is a fall Sunday at Soldier Field. We recommend a Sept./Oct. game if you don’t feel like freezing your ass off. Then again, that’s the best part of the game for some people. Chicago is weird that way. For extra fun, take the Reggie’s bus to and from the action.

Soldier Field

Hit a Bears game, obviously Soldier Field Despite the low expectations of success on the field this year, nothing can take away from the ambiance that is a fall Sunday at Soldier Field. We recommend a Sept./Oct. game if you don’t feel like freezing your ass off. Then again, that’s the best part of the game for some people. Chicago is weird that way. For extra fun, take the Reggie’s bus to and from the action.

Flickr/clarkmaxwell

Date

Event

Location

Oct 15-31

Peep some leaves (that’s what they call it) If you’ve never been, Morton Arboretum is a fall must-visit for nature fans. But if you’d rather not trek out to Lisle to peep leaves, there’s plenty of fall color to see in town. We recommend places like the underrated Milton Lee Olive Park, a stroll through Lincoln Park (the actual park), or just a simple meander through your 'hood before the leaves disappear and the sky turns grey for the next six months.

Morton Arboretum

Peep some leaves (that’s what they call it) Morton Arboretum If you’ve never been, Morton Arboretum is a fall must-visit for nature fans. But if you’d rather not trek out to Lisle to peep leaves, there’s plenty of fall color to see in town. We recommend places like the underrated Milton Lee Olive Park, a stroll through Lincoln Park (the actual park), or just a simple meander through your 'hood before the leaves disappear and the sky turns grey for the next six months.

Courtesy of Andersonville Dessert Crawl

Date

Event

Location

Oct 25 Sun

9th Annual Andersonville Dessert Crawl Who said trick-or-treating is just for kids? We teamed up with Hyundai for a tasty Sunday recommendation:

Avoid the incessant doorbells and go gourmet trick-or-treating (last year there was blood orange mousse and butterscotch panna cotta!) on the Andersonville Dessert Crawl. It’s the perfect way to soothe your adult sweet tooth.

Andersonville

9th Annual Andersonville Dessert Crawl Andersonville Who said trick-or-treating is just for kids? We teamed up with Hyundai for a tasty Sunday recommendation:

Avoid the incessant doorbells and go gourmet trick-or-treating (last year there was blood orange mousse and butterscotch panna cotta!) on the Andersonville Dessert Crawl. It’s the perfect way to soothe your adult sweet tooth.

Flickr/Rubbertoe

Date

Event

Location

Oct 30 Fri

Dress like a Halloween weirdo and freak people out in Toyota Park Dress like a slut, dress like a superhero, dress like Donald Trump. It doesn’t matter, as long as it’s weird. Halloween parties abound in Chicago but perhaps no event is more equipped to deal with the Halloween mania this year than Freaky Deaky, a three-day orgy of EDM and neon going down in Toyota Park with the help of Bassnectar, 2 Chainz, and Pretty Lights.

Toyota Park

Dress like a Halloween weirdo and freak people out in Toyota Park Toyota Park Dress like a slut, dress like a superhero, dress like Donald Trump. It doesn’t matter, as long as it’s weird. Halloween parties abound in Chicago but perhaps no event is more equipped to deal with the Halloween mania this year than Freaky Deaky, a three-day orgy of EDM and neon going down in Toyota Park with the help of Bassnectar, 2 Chainz, and Pretty Lights.

Flickr/Luis Ramirez

Date

Event

Location

Nov 26 Thu

Get someone else to cook your turkey The only thing anyone wants to do less than travel to your second cousin’s house for Thanksgiving is to cook your own Thanksgiving dinner. Luckily, you can act like a hero by bringing the bird from local Thanksgiving takeout joints like Frontier, Parson’s, and Smoke Daddy. All you have to do is act like you spent all day in the kitchen and take all the credit. Nice right?

Mutliple venues

Get someone else to cook your turkey Mutliple venues The only thing anyone wants to do less than travel to your second cousin’s house for Thanksgiving is to cook your own Thanksgiving dinner. Luckily, you can act like a hero by bringing the bird from local Thanksgiving takeout joints like Frontier, Parson’s, and Smoke Daddy. All you have to do is act like you spent all day in the kitchen and take all the credit. Nice right?

Date

Event

Location

Nov 27 Fri

Stand in line to await the release of Bourbon County Stout While there is debate about which pumpkin beer is best, there is no debate about Bourbon County Stout, a consensus pick as one of the finest beers in the world. It’s so good that you’ll happily wait in line for hours in anticipation of its release this November. What else you gonna do, go holiday shopping?

Liquor stores around Chicagoland

Stand in line to await the release of Bourbon County Stout Liquor stores around Chicagoland While there is debate about which pumpkin beer is best, there is no debate about Bourbon County Stout, a consensus pick as one of the finest beers in the world. It’s so good that you’ll happily wait in line for hours in anticipation of its release this November. What else you gonna do, go holiday shopping?

Flickr/Greg Lilly

Date

Event

Location

Nov 28 Sat

Take a fall road trip to see some college football Fall in Big Ten country is synonymous with college football. And for good reason. Not only is the conference home of the defending national champs, it is also home to the three biggest football stadiums in the world (Michigan, Penn State, Ohio State). All of them pack 100K+ people in most fall Saturdays, which is about the best way you can spend most fall Saturdays.

Ann Arbor, Michigan

Take a fall road trip to see some college football Ann Arbor, Michigan Fall in Big Ten country is synonymous with college football. And for good reason. Not only is the conference home of the defending national champs, it is also home to the three biggest football stadiums in the world (Michigan, Penn State, Ohio State). All of them pack 100K+ people in most fall Saturdays, which is about the best way you can spend most fall Saturdays.

Date

Event

Location

TBA

Find some stupid excuse to drink beer in a Santa suit From Santacon to the Twelve Bars of Christmas (TBOX) to this year’s Santa Hustle, there’s always some dumb excuse for you to throw on a Santa suit and act like an idiot with a drink in hand. Call it holiday tradition. Thank you Jesus.

Various locations

Find some stupid excuse to drink beer in a Santa suit Various locations From Santacon to the Twelve Bars of Christmas (TBOX) to this year’s Santa Hustle, there’s always some dumb excuse for you to throw on a Santa suit and act like an idiot with a drink in hand. Call it holiday tradition. Thank you Jesus.

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