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Fall bucketlist lead art

Chantal Bennett Illustration

Everything you should do this fall is on this list

This story was updated for 2023 by Samantha Callender, Courtney Kueppers and Mendy Kong.

The good news: Fall is striking in the Great Lakes region of the Midwest.

As any seasoned Chicagoan knows, now is the time to take advantage of all the Midwest has to offer, from the crisp, temperate air to the enchanting fall foliage. You can stay close — a recommended site for leaf peeping is The Morton Arboretum, which this year brings back its family-friendly Scarecrow Trail (daily in October) — or travel farther afield.

Better yet, there are enough weekends left to plan multiple adventures.

WBEZ put together a jam-packed guide to get you started. Call it a bucket list if you want, or simply a list of researched suggestions that come highly recommended. Whether you are eyeing an afternoon or a full-day trip, it’s intended to help you enjoy the best the greater Chicago area has to offer, from cider mills to apple picking to hiking.

Don’t see something on the list that you think belongs here? Tell us #WBEZFallOutdoors or email us at (use the subject line “Fall Bucket List”). Also, we recommended calling each site before your visit, as hours may change.

  1. Pumpkin patches
  2. Corn mazes
  3. Apple picking
  4. Apple cider drinking
  5. Leaf peeping drives
  6. Spooky screenings
  7. Oktoberfests -- and a sober fest
  8. Fall gardening
  9. Farm dinners
  10. Hiking and kayaking


Pumpkin Patching

Is there anything more ubiquitous in fall than a pumpkin? Luckily, there are plenty of U-Pick and pre-picked options not far from Chicago. Many patches have loads of activities all season long in addition to picking pumpkins, from hayrides to petting zoos. Pricing varies.

Sonny Acres Farm in West Chicago has been in operation since 1883, but in 2019 it was acquired by the Joyaux and Fontana families. They’ve expanded the already bountiful attractions, which include a petting zoo, outdoor kitchen, amusement rides, haunted barn, hayrides and wildly popular apple cider donuts. By mid-September, the farm was already filled with pumpkins, with different varieties coming in throughout the early fall. 29W310 North Ave., West Chicago; 10 a.m. to 6 p.m. through Oct. 29. Cost varies.

Pumpkin patch

A friendly face welcomes visitors to Sonny Acres Farm.

Courtesy of Sonny Acres Farm

Goebbert’s Farm Pingree Grove offers U-Pick pumpkins every day of the week, depending on the weather. Through Halloween, you can also purchase a ticket for their Fall Festival, which includes wagon rides, a corn maze, a giant pumpkin slide and loads of other family activities. 42W813 Reinking Road, Pingree Grove; U-Pick fields open 8 a.m. to 6 p.m. daily, weather dependent; text PICK to 844-916-4618 for updates on U-Pick field status. Cost varies.

The 40-acre Abbey Farms in Aurora is open Wednesday-Sunday through Oct. 30, offering both pre-picked and U-Pick options. Tickets to their Pumpkin Daze festivities include a corn maze, jumping pillow, go-karts and a weekend petting zoo. 2855 Hart Road, Aurora; Wednesdays-Sundays 10 a.m. to 6 p.m. Open 10 a.m. to 10 p.m. Saturdays in October. $12-$23.

All Seasons Orchard in Woodstock is an apple and pumpkin farm with an expanded “family fun” area that includes a ropes course, corn maze, zipline, sunflower field and petting zoo. 14510 IL Route 176, Woodstock; weekdays 10 a.m. to 5 p.m. and Saturdays and Sundays 10 a.m. to 6 p.m. A combo ticket for U-pick and the family fun area is $24 per person on weekdays and $32 on weekends.

An illustration of a corn maze

Chantal Bennett Illustration

Corn Mazes

Illinois claims the second highest corn production of any state, with 11 million acres allocated to the crop, so it makes sense it’s also home to its fair share of corn mazes. This year there’s everything from spooky themes timed for Halloween to an intricate design with a Jurassic Park theme. Go for the maze, stay for the apple cider doughnuts and hayrides.

Richardson Farm in Spring Grove has one of the best-known corn mazes around. Each year, the farm chooses a different theme for their epic maze — this year’s pays homage to Jurassic Park, with an insanely detailed design featuring over nine miles of trail on a path that winds through 28 acres of corn. 909 English Prairie Road, Spring Grove; open 3 to 9 p.m. Thursday, 10 a.m. to 11 p.m. Fridays and Saturdays and noon to 9 p.m. Sundays through Oct. 29. $18-30.

A child running through a corn maze

Illinois boasts 11 million acres of corn and several noteworthy mazes.

Rich Hein / Chicago Sun-Times

Besides U-pick pumpkins and apples, Jonamac Orchard serves up a corn maze that usually takes about an hour to complete. This year’s design celebrates farming families — but if you’re in the mood for something spooky, select dates feature a haunted version of the maze. The latter is recommended for ages 13 and up. 19412 Shabbona Road, Malta; open noon-5:30 p.m. Friday, 9 a.m. to 5:30 p.m. Saturdays and Sundays. $5 to $8 for general admission.

About an hour north of Chicago, the corn maze at Kroll’s Fall Harvest Farm in Waukegan comes with its own virtual app, equipped with a GPS. Kroll’s corn maze this year will have a goat theme; while you’re there, be sure to stop by their petting zoo and take a hayride. 13236 W. Townline Road, Waukegan; open Monday and Friday 10 a.m. to 8 p.m., Wednesday-Thursday 1 to 8 p.m., timed entry tickets required on Saturday and Sunday. $4-14.

So it’s technically not a corn maze, but the Morton Arboretum’s annual Scarecrow Trail is a not-to-be-missed, family-friendly event that features a walking path lined with scarecrows. The scarecrows are made by local scout troops, and visitors can vote for their favorite after their walk. Morton Arboretum, Meadow Lake Trail, near the Visitor Center, 4100 Illinois Route 53, Lisle; daily in October, 7 a.m. to sunset. $9-17, included with timed entry ticket.

apple picking separator

Chantal Bennett Illustration

Apple Picking

Apple picking

There are several apple orchards within a short drive of Chicago. Go for the fruit, stay for the apple cider doughnuts.

Charmaine Runes for WBEZ

Whether you are stocking up on fruit for winter pies or just looking to get outside and be close with nature, apple picking is a quintessential fall activity in the region. Most area orchards tend to grow multiple varieties, with what’s available waxing and waning as the weeks progress -- so before you go, be sure and check the orchard’s social media pages or call ahead to see what’s available that day.

Click here for 10 of the best area spots for apple picking, including several within an hour or two’s drive from Chicago’s Loop. The list also includes farther flung orchards in Wisconsin, Indiana and Michigan that make for great day trips from Chicago.

U-pick apples, cider and donuts: Here are 10 of the best places to go around Chicago

Apple cider toasting

Chantal Bennett Illustration

Apple Cider sampling

There are dozens of cider mills and cideries across the region making use of local apples, and we’ve put together a map of seven of the best, from right here in Chicago to Madison to southwest Michigan.

Besides tastings of unique small batch offerings, several cideries on our list also offer a menu of activities that make them great day destinations, from farm tours to concerts. Maybe it’s the farm vibe, but the destinations also tend to be kid- and pup-friendly. But it’s always wise to check hours and specifics before you set out, since cideries are small businesses and things can change.

Click here for our seven-mill cider tour around the Midwest, complete with a map and hours and details.

The great cider road trip: Seven Midwest cideries worthy of a visit

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Chantal Bennett Illustration

Leaf Peeping Drives

Autumn is one of the most beautiful times of year in the Midwest — that the changing colors of the leaves are fleeting makes the season all the more special. Each state has its own beloved drives for catching the fall foliage, with experts saying that Illinois will reach peak autumnal foliage mid-October. Below are three noteworthy routes.

About forty minutes’ drive from Milwaukee, the Basilica and National Shrine of Mary Help of Christians at Holy Hill sits atop one of Wisconsin’s highest points; in the fall, a scenic tower at the church affords spectacular views of autumn’s changing colors. The site sits inside Kettle Moraine State Park, where you can embark on a 115-mile scenic drive and glimpse Wisconsin’s most beautiful geology. (Suggested GPS point: 1525 Carmel Road, Hubertus, Wis. 53033; tower is open Monday to Saturday 9 a.m. to 5:30 p.m. in October, and Sunday 1:30 to 4:40 p.m.)

fall colors

Explore all the beautiful colors fall has to offer at the Morton Arboretum.

Courtesy of the Morton Arboretum

For drivers craving a day trip and maybe seeking out a quaint place to stay for the night, this route takes you along Lake Michigan, from Warren Dunes State Park to Benton Harbor, and then loops inland for a drive through some of Southwestern Michigan’s most picturesque towns. Embarking during the month of October guarantees the best foliage views; along the way, you can stop off at attractions like the Fernwood Botanical Gardens & Nature Preserve in Niles or the Warner Vineyards Winery, on the banks of the Paw Paw River. (Suggested GPS point: 224 W. Buffalo St., New Buffalo, Mich.)

This scenic route for weekenders begins in Hartford in Southern Illinois on the bank of the Mississippi River and takes drivers northwest along stunning river scenes before ending at Pere Marquette State Park. The byway sits about five hours from Chicago, an area loaded with history and majestic natural areas, such as the onetime home of Lewis and Clark and the Riverlands Migratory Bird Sanctuary. (Suggested GPS point: 100 W. Broadway, Alton, Ill.)E

The Music Box

The Music Box of Horrors returns in October 2023.

Tyler LaRiviere/Chicago Sun-Times

Spooky Screenings

Movie marathons, a popular 2023 release and a screening of Nosferatu with a live doom funk band are among the offerings.

The Davis Theater in Lincoln Square will again host the Massacre, a 14-hour movie marathon whose vibe is all in the title. Held on Sept. 30 through the wee hours, the series kicks off with Nosferatu at noon, and films such as Slumber Party Massacre, Monster Cereal Break and Spider Baby are on the lineup, among others. 4614 N. Lincoln Ave., Chicago. $30.

The Music Box of Horrors series returns on Oct. 21st with a 24-hour movie marathon that features high camp (Piranha II: the Spawning) and overlooked gems (Burnt Offerings) across the 1970s, 80s and 90s. 3733 N. Southport, Chicago. Festival passes are $30 through Oct. 20 when they go up to $35; a “half-marathon” option is available.

The indie movie house Facets will host a series of horror-themed film weekends that feature new filmmakers and obscure screenings. Starting Friday, Oct. 13th through the weekend, the House of Movie Monsters presents SUPER-HORROR-RAMA! a bazaar of pop-up horror vendors and themed screenings, including a trio of 1960s-era witch-themed movies (City of the Dead, The Witches Mountain and Burn, Burn, Burn) on Oct. 14. 1517 W. Fullerton Ave, Chicago. Tickets range from $12 to $40.

The Chicago Horror Film Festival will bring its selections from the best new indie horror films to Facets on Oct. 21 and 22nd. Tickets are $10.

Facets will screen Talk to Me, the breakout Australian horror film of the year, about a disembodied hand with an otherworldly connect from Oct. 26-29. $12 for non-members, $10 for members.

WBEZ will host a Halloween screening of the 1922 silent classic Nosferatu, accompanied by a live original score by the Chicago doom funk band Gramps the Vamp, on Oct. 28 at the Studebaker Theater, one of the city’s oldest cultural venues. The film will be presented in its original color restoration with German intertitles. The Studebaker Theater in the Fine Arts Building, 410 S. Michigan Ave., Chicago. Tickets are $30.


At the turn of the 20th century, people of German descent made up the largest ethnic group in Chicago — that long lineage is one reason the region now boasts numerous Oktoberfest celebrations. Originally conceived as a people’s festival in Munich, today the tradition lives on in iterations throughout Chicagoland, featuring plenty of beer, hearty food and German music.

St. Alphonsus was founded by German immigrants in 1882; more than 100 years later, the church continues to honor that history by throwing an epic annual Oktoberfest. Local bands, such as School of Rock and Dancing Queen, play Friday and Saturday, when you can also purchase tickets for a craft beer tasting featuring 15 different brews. 1429 W. Wellington Ave.; Sept. 22 to 24. Tickets start at $40.

Cloud gate fall

Take a stroll around Millenium park this fall for magical moments.

Daniel Bartolo

Naperville celebrates the Oktoberfest tradition at Naper Settlement on Oct. 6 -. 7. Live polka and rock bands will play both days, and a professional pumpkin-carver will be on site; guests can also take part in lawn games and a stein-holding contest. Enjoy German food and beverages no matter the elements — all activities take place under a heated tent. 523 S. Webster, Naperville; Friday 5 to 10 p.m., Saturday 3 to 10 p.m. $20.

For an Oktoberfest celebration without the booze that’s still adults-only, Lincoln Park Zoo and Chicago AF are offering up Oksoberfest. This year’s inaugural event is for those 21 to experience the zoo after-hours without the kids and crowds. Organizers will serve up non-alcoholic beers and zero-proof cocktails in addition to classic snacks such as wurst and soft pretzels. Lawn games and live music will keep the good vibes going without the hangover. 2400 N. Cannon Drive, Chicago. Tickets start at $25.

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Fall might not seem like an obvious time to think about gardening, but it’s actually a great time to save seeds, plan next year’s planting or extend this year’s growing season.

Learn how to take your flowers from garden to table centerpiece at the From Garden to Vase: Autumn Flowers workshop at the Chicago Botanical Gardens. They’ll teach you how to identify plants that are ideal for arrangements, how to best remove them from your garden, and how to properly cut them. Led by Tim Pollak, an outdoor floriculturist, you’ll also learn how to beautifully arrange stems for a stunning arrangement right from your own backyard. 1000 Lake Cook Road, Glencoe. Tickets are $49 for members and $62 for non-members.

Botanic garden

Malott Japanese Garden at the Chicago Botanic Garden features a beautiful fall rainbow.

Courtesy of the Chicago Botanic Garden

Get into the ancient art of bonsai sculpting with this workshop that’s perfect for beginner growers at the Bonsai Basics: A Journey into the Art of Miniature Trees. Held every Saturday through Feb. 17, 2024, the workshop will feature experienced instructors who will guide you through the techniques for selecting, trimming, and sculpting bonsai trees that by the end of the program you’ll be able to take home and confidently care for. 917 West 18th St., Chicago. $55.

Find some inspiration for your own garden at the Center on Halsted’s Rooftop Garden Tour (next tours are Sept. 23 and Oct. 12). Learn and explore rooftop pollinators and vegetable gardens and explore over 85 plant species native to Chicago that attract Monarch butterflies. The tour will also feature an exploration of the veggie garden that supports the Center’s Silver Fork Culinary Arts training program and seniors at the Center on Addison. Participation is free with an RSVP. 3656 N. Halsted St., Chicago. Free, but donation accepted.

If you don’t want to commit to having your own garden to tend but still want to get your hands dirty for a day, spend some time volunteering at the Star Farms Volunteer Event. Located in the Back of the Yards, this nonprofit urban farm and landscaping service will open their gates so the community can help them with a variety of gardening tasks around the plot. After a season of farmer’s markets and pop-ups, the growers will teach some fundamentals of gardening with some hands-on learning opportunities. 5138 S. Carpenter Ave, Chicago. $5.

Calling all want-to-be “plant parents” — Cultivate Urban Rainforest & Gallery will be hosting workshops on the first Sunday of each month to teach a Plant Parenthood workshop. Here, you’ll learn skills like finding/creating proper light and how to regulate humidity in your home to take optimal care of your plants. The workshop will also have an interactive Q&A session where specific questions can be answered (and even demonstrated). 704 Main St., Evanston. $25.

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Chantal Bennett Illustration

Farm Dinners

Fall harvest season is the best time to enjoy the bounty of the land, and farm dinners are the perfect way to enjoy locally grown food. The fact that you’re helping to support the hard work of local farmers is icing on the cake.

Grace United Church of Christ hosts a multi-course dinner on It Takes A Village Community farm on Sept. 23. Tour the farm and enjoy drinks and a multi-course dinner featuring homegrown organic produce. All proceeds benefit the farm, which offers free programming and job training. (2500 223rd St., Sauk Village; Sept. 23, 5:30 p.m. to 8 p.m. $60)

If you’re looking to stay in the city, Big Delicious Planet is hosting an Urban Farm Dinner series throughout October. With 77 garden beds, long farm tables, and pergolas, you’ll feel like you’ve been transported out of Chicago to Napa Valley. The night starts off with passed appetizers and cocktails before a salad course, family-style dinner, and dessert. The dinner features the organic urban farm’s daily harvest as well as a variety of local purveyors. 412 N Wolcott Ave., Chicago. From $95.

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Chantal Bennett Illustration

Hiking, kayaking and hikes near breweries

Fall is the pinnacle of hiking season in the Great Lakes region due to the beauty of the changing leaves, dissipating mosquito and tick populations and that crispness to the air.

When it comes to kayaking, dramatic improvements in water quality during the past several decades of conservation advocacy have made excursions on regional waters healthier and more pleasurable. Of course, there is the well-trekked Chicago River, which has several launch spots for kayaks and rental companies galore — but northern Illinois also offers dozens of lakes, rivers and other water bodies to paddle within an hour or two of the city.

Here are three lists that offer plenty of adventure for you to squeeze in this fall, or use to start planning spring outings.

  • This list of 20 great Midwest hikes to do before winter sets in includes short treks perfect for families (including those in Indiana Dunes National Park and the Palos Trail System) as well as longer treks for the adventurous who crave uncongested trails and the beauty of prairie.

  • Will hike for beer! Earlier this year, we assembled this list of hikes with taprooms near their trailheads. Some are close to Chicago, while others will take you farther afield to Wisconsin and Michigan. It includes beer recommendations.

  • For kayaking and canoeing, click here to find our recommended list of 14 waterways for paddling in the area. It includes everything from still water recommendations, such as the Skokie Lagoons north of the city, to easily accessible rivers such as the DuPage and the Des Plaines. For moving water, don’t forget to check water levels before you go. Find Illinois river information here.


Take advantage of Illinois waterways before they freeze.

Courtesy of Liina Raud/Openlands

This story was originally published in September 2022. Hours, locations and offerings have been updated for 2023.

Updated: The pricing for SUPER-HORROR-RAMA! was updated after publication. Tickets are $12 to $40.

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