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Published August 28, 2023

The Best Farms, Pumpkin Patches, and Fall Festivals in and Around Chicago

Celebrate the season with these fun fall activities! 🍁🎃

by Chicago Bucket List


The leaves are changing, the air is getting crisp, and fall is almost here! There’s no better way to celebrate the season than with visits to the countryside for freshly picked apples and pumpkins, thrilling haunted houses, and cozy hayrides and campfires.

Bucketlisters is here to help you make the most of fall with our list of the best farms, pumpkin patches, and festivals in Chicago. Get your flannel ready and get exploring!

Chicago Fall Festivals and Parades

Oktoberfest Chicago

Oktoberfest is back at St. Alphonsus' annual Craft Beer Tasting evenings on September 22 and 23! Choose 15 samples from 28 different local, imported, or seasonal brews, then head outside the Festival Hall and enjoy music, food, games, and activities at Oktoberfest Chicago!

Where: St. Alphonsus Downstairs Beer Hall: 1429 W Wellington Ave.
More information.


St Alphonsus Church, West Wellington Avenue, Chicago, IL, USA
Craft Beer Tasting at Oktoberfest Chicago
Starting at $35

Book now


Lincoln Park Wine Fest

On October 6 though October 8, Lincoln Park Wine Fest will transform tranquil Jonquil Park into an open-air market with wine, sangria, and sparkling tastings from 25+ high-end worldwide varieties. Vino, Wein, Vin, and did we say sangria?

Where: Jonquil Park: 1001 W Wrightwood Ave., Chicago, IL
More information.


1001 W Wrightwood Ave, Chicago, Illinois, USA
Lincoln Park Wine Fest
Starting at $42

Book now


Lincoln Park Zoo Fall Fest

The fall fun doesn’t stop at Lincoln Park Zoo’s Fall Fest, running every weekend from September 29 through October 29. The zoo is always free to visit the animals, and during the fall festival, visitors can buy tickets for experiences including the Ferris Wheel, Pumpkin Walk, Harvest Maze, and more.

Check out the Haunted History Tours on Tuesdays and Wednesdays in October to learn about the zoo’s haunted history as a former cemetery, or enjoy the park after dark at the Adult's Night Out Howl-O-Ween event on October 26.

Where: 2400 N. Cannon Drive, Chicago, IL
More information.


Lincoln Square Annual Apple Fest

The Ravenswood community will usher in the fall season on September 30 and October 1 this year with apple-inspired food and beverages. Grab an apple brat or apple grilled cheese, and top it off with a slice of classic apple pie or apple waffles. You can also take home bushels of fresh apples, apple butter, syrup, cider, and more to enjoy all season long!

Where: Lincoln Avenue between Lawrence and Wilson, Chicago, IL
More information.


Chicago Food Truck Festival

Experience Chicago's most diverse food truck lineup at the tenth annual Food Truck Festival. Taking place on October 7 and 8 this year, the festival will feature dozens of the city's top food vendors. Try everything from deep-dish pizza to curly fries to chicken and waffles all within walking distance! Seating is limited, but feel free to bring your own.

Pro-Tip: Rather than try to find parking, use a rideshare service to get there. The festival offers an Uber and Lyft credit to attendees. Find it on their FAQ page.

Where: La Bagh Woods, Chicago, IL
More information.


Arts in the Dark Halloween Parade

Arts in the Dark is an organization that celebrates the artistry of Halloween, and you won’t want to miss the killer Halloween parade! On October 21, the Ninth Annual Arts in the Dark Halloween Parade will take place in the heart of Chicago with a traditional parade featuring one-of-a-kind floats, puppets, and other performances.

Where: State Street (moving from Lake towards Van Buren), Chicago, IL
More information.


Chicago Pizza Summit

Get ready for a day of all things pizza as the Chicago Pizza Summit returns after a two-year hiatus on October 15! This beloved Windy City tradition is back, celebrating Chicago's deep love for pizza with a day full of delicious slices from Chicago's finest pizzerias and exciting attractions like a surprise keynote speaker, a Pizza Tattoo Parlor, and a Pizza Themed Best Dressed contest!

Where: Royal Palms Shuffleboard: 1750 N Milwaukee Ave, Chicago, IL
More information.


Royal Palms Chicago, 1750 N Milwaukee Ave, Chicago, IL 60647, USA
Chicago Pizza Summit 2023
Starting at $50

Book now


Rosemont Family Fall Fest

Bring the whole family to welcome fall with a day of fun at Rosemont’s annual Family Fall Fest, hosted on Saturday, September 17. The event will feature festive free activities, including a bounce house, a petting zoo, face painting, pumpkins, balloon sculptors, and more. There will also be live music from the kid-friendly “ScribbleMonster” band to get you grooving. 

Where: Parkway Bank Park, 5501 Park Place, Rosemont, IL
More information.

Farms and Pumpkin Patches Near Chicago

County Line Orchard

Head to County Line Orchard for your fix of fall activities. The orchard offers U-pick apples, pumpkins, and sunflowers—tractor ride included! While you’re there, check out the corn maze or take the kiddos on the Moo Choo tractor train.

On Friday and Saturday evenings, groups of up to 30 people can book a campfire & hayride experience to spend a festive fall evening around a crackling fire. You can also catch live music during the Orchard’s Barnyard Jams series, featuring a rotating lineup of bands playing each weekend.

Where: 200 S. County Line Rd, Hobart, IN
More information.


Jonamac Orchard

Jonamac Orchard is open seven days a week for apple picking and has special fall-themed events throughout the season. Check out Fall Festival Days every Saturday and Sunday from September 2 through October 30, where the whole family can enjoy attractions like a bubble barn, corn cribs, a petting zoo, a play tractor, a straw bale pile, and more.

Wander through the corn maze (haunted on Friday and Saturday nights), grab a gourd from the pumpkin patch, and don't forget to snag a caramel apple and a cup of cider before you head out!

Where:19412 Shabbona Rd, Malta, IL
More information.


Apple Holler

Escape to the countryside for a quintessential fall outing at Apple Holler farm, where you can head into the orchard to pick your choice of 30+ varieties of apples. Stop in the farm store for fresh homemade treats like apple cider donuts and caramel apples, or hit up the Biergarten, serving up Wisconsin brews, including a hard cider made with apples straight from the farm.

You can even take a horse-drawn carriage tour around the property to learn about farm life and finish with a campfire complete with s’mores and fresh apple cider. 

Where: 5006 South Sylvania Ave, Sturtevant, WI
More information.


History Tours and Haunted Hayrides at Blackberry Farm

Enjoy a day trip to Blackberry Farm, a living history museum that features several exhibits on pioneer life, plus activities including pony rides and paddle boating. On weekends during October, stop by the farm for Pumpkin Weekends or their popular Haunted Hayrides, complete with a bonfire and s’mores.

Where: 100 S. Barnes Road, Aurora, IL
More information.


Harvest Tyme Family Farm

Head to Harvest Tyme Family Farm for their Fall Festival, running every weekend from September 30 through October 29. At the farm, you’ll find a pumpkin patch, corn mazes, a hayride, a petting zoo, amusement rides, plus a dino-themed corn maze with a lookout bridge that gives you an amazing view of the whole maze (a great photo-op spot).

Don’t miss the farm’s Pumpkin Glow Trail, a glow-in-the-dark pumpkin experience featuring over 1,000 jack-o-lanterns and lighted displays.

Where: 17904 Grant St, Lowell, IN
More information.


Sonny Acres Farm

Sonny Acres is a family-owned farm that has hosted a Fall Festival with fun for the whole family for decades. In addition to a classic pumpkin patch, the farm has a variety of attractions, including a petting zoo, a giant jumping pillow, a rollercoaster, and a train that winds around the property.

Thrillseekers won’t want to miss their Haunted Barn and Haunted Wagon Ride experience, opening on September 30. Don’t forget to stop at their Farm Fresh Store to find seasonal produce, sweet treats, and country home decor.

Where: 29W310 North Ave., West Chicago, IL
More information.


Jerry Smith Pumpkin Farm

If you’re looking to pick the perfect pumpkin to carve, head to the pick-your-own pumpkin patch at Jerry Smith farm. Once you’ve picked out your gourd, take some time to explore the farm, and you’ll find a display of over two dozen hand-painted pumpkins, plus several activities, including a petting zoo, giant bounce pad, a 6-acre corn maze, hayrides, and a tire mountain.

If you’re in the mood for a scare, check out the Dr. Destruction’s Haunted Manor event, open from September 16 through October 31. Don’t skip the farm’s famous frosted cookies!

Where: 7150 18th Street (Highway L) Kenosha, WI
More information.


Odyssey Fun Farm

Odyssey Fun Farm is all about corn-y fun—in the best way. They’ve got a bunch of corn-themed fall activities, including a themed corn maze and a corn “sandbox,” plus other fall fun, including a climbable hay mountain, hay rides, pumpkin picking, and attractions like ziplining and a pillow jump. You won’t want to miss their corn cannon, which lets you use high-powered air cannons to shoot corn at targets!

Where: 18900 Oak Park Ave., Tinley Park, IL
More information.


Bengtson’s Pumpkin Farm & Fall Festival

Experience an action-packed day of fall fun at Bengton’s Pumpkin Farm. In addition to a pumpkin patch, the farm has 13 rides and attractions, including roller coasters, swings, and trains, a haunted barn, a petting zoo, and even pig races. The farm serves up tasty treats, including apple cider donuts, sweet corn, BBQ, and kettle corn. Definitely don’t forget to check out the crowd-favorite Pumpkin Chucker to watch pumpkins catapult through the air at high speed. 

Where: 13341 West 151st St., Homer Glen, IL
More information.


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