October in Chicago here we come! Let’s get ahead on the Halloween festivities and enjoy our cider and pumpkin season!

women doing job in field in daytime
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Jack’s Pumpkin Pop-Up

Located on a two-acre parcel just west of Goose Island, Jack’s Pumpkin Pop-Up eliminates the need for a suburban excursion by delivering an abundance of autumn entertainment to the heart of the city. This includes a sprawling corn maze, over 10,000 pumpkins, axe throwing, carnival games, food trucks, enchanting orange light exhibitions, and a variety of other seasonal delights. A standard admission ticket grants you entry to this pop-up extravaganza, while additional options are available for those looking to purchase a pumpkin to take home, enjoy a drink at one of the bars, or try their hand at axe throwing.

Until Nov 4th

a dog sitting near the pumpkins
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Fall Fest

Explore the enchanting autumn realm—from selecting the ideal pumpkin to savoring the familiar fragrances of warm cider and toasted s’mores—by joining Lincoln Park Zoo’s ninth annual Fall Fest. This beloved, family-friendly celebration ushers in the harvest season right in the heart of Chicago, running from September to October.

This year’s festivities encompass various paid attractions sprinkled throughout the zoo, including an exhilarating Fun Slide, a maze teeming with pumpkins, bouncy inflatables, and much more. Attendees can also relish in complimentary musical performances, captivating story sessions, skilled pumpkin sculptors, a charming pumpkin patch, and autumn-inspired activities for the animals. Each weekend promises fresh delights!

Lincoln Park Zoo’s Fall Fest is an admission-free event, and no registration is necessary.

September 29–October 29

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Oktoberfest at The Northman Beer & Cider Garden

Join in the Oktoberfest revelry during three consecutive weekends at The Northman Beer & Cider Garden, where a medley of festivities awaits along the Riverwalk this September and early October. The entertainment lineup boasts an array of performers, including Sara Jean Stevens and Whiskey Bob & The 12 Steps, along with Alpine Thunder Live, a German folk-pop ensemble that’s set to commandeer the bar’s Pergola State with two captivating sets on September 7th and October 7th.

Until Oct. 8th

Enjoy Chicago! ~ Juliana