More fall fun: Apple picking, hayrides and a pumpkin-eating dinosaur

There’s something about fall in Chicago that makes even the most devoted city dweller want to trade skyscrapers for apple orchards, swap sidewalks for pumpkin patches and spend a Saturday searching for the perfect pumpkin. Add a little cider, a hayride, a corn maze and perhaps a caramel apple or two, and suddenly a day in the country sounds like a very good idea.

Fortunately, you don’t have to travel far from the city to find a little autumn magic. From family-friendly farms and sprawling corn mazes to apple orchards and seasonal festivals, the Chicago area offers plenty of ways to celebrate the season.

Here are some places to put on your fall calendar, whether you're planning a family outing, a date, a friends' day in the country or simply looking for an excuse to indulge in a cider doughnut.

Apple picking and pumpkin patches

For those who want to fill a bag with fresh apples, find a pumpkin to take home or turn the outing into a full day of farm fun.

1. Kuipers Family Farm

Maple Park, Illinois

Kuipers Family Farm combines apple picking with its Pumpkin FunFarm, making it a destination for anyone who wants more than a quick stop at a roadside patch. The orchard grows numerous apple varieties, and the farm also offers seasonal activities and a bakery. Its Fall Harvest Fest runs now through Nov. 1, 2026.

More information: Kuipers Family Farm website 

2. All Seasons Orchard

Woodstock, Illinois

All Seasons Orchard offers pick-your-own apples, a pumpkin patch, a themed corn maze and a Barnyard play area featuring more than 30 activities. Wagon rides take visitors to the orchard, where Honeycrisp and other varieties await. Pumpkin picking begins in mid-September. The 2026 season runs now through Nov. 1, with hours varying by day.

More information: All Seasons Orchard website 

3. Keller’s Farmstand

Oswego, Illinois

Keller’s Farmstand offers pick-your-own apples alongside pumpkins and seasonal weekend activities. It’s a good choice for a relaxed farm outing, with the added temptation of apple cider doughnuts and cider floats. Check the farm’s current details for apple availability and fall activities.

More information: Keller’s Farmstand website 

4. Stade’s Farm & Market

McHenry, Illinois

Stade’s Farm & Market brings together apple picking, pumpkins, sunflowers and a corn maze during its Shades of Autumn season. The farm’s fall festivities include seasonal attractions and activities. Check the current calendar for operating dates and apple-picking availability.

More information: Stade’s Farm & Market website 

5. Goebbert’s Farm

Pingree Grove, Illinois

Goebbert’s is known for its pumpkin-themed displays, animal areas, wagon rides and signature Pumpkin-Eating Dinosaur. The farm’s Fall Fest offers plenty to keep younger visitors occupied, making it a popular choice for families looking to turn pumpkin shopping into a full outing.

More information: Goebbert’s Farm website 

6. Bengtson’s Pumpkin Fest

Homer Glen, Illinois

Bengtson’s turns pumpkin season into a full day of entertainment, with rides, shows, animals, photo opportunities and its Pumpkin Chucker attraction. It’s a lively option for families looking to make a whole event of their pumpkin outing. Check the festival’s schedule for dates, hours and ticket information.

More information: Bengtson’s Pumpkin Fest website 

7. Heap’s Giant Pumpkin Farm

Minooka, Illinois

Heap’s offers a 25-acre pumpkin patch with pumpkins, gourds and squash, along with hayrides, mazes and other farm activities. It also offers a separate after-dark haunted corn maze experience on select nights. Check its calendar for daytime and evening activities.

More information: Heap’s Giant Pumpkin Farm website 

8. Cody’s Farm & Orchard

Marengo, Illinois

Cody’s offers a farm market, apple orchard and pumpkin picking on select fall weekends. The farm advertises free admission and parking, along with free hayrides to the pumpkin patch. Check its current schedule and picking conditions before visiting.

More information: Cody’s Farm & Orchard website 

9. Richardson Adventure Farm

909 English Prairie Road, Spring Grove, Illinois

If you’re ready to get lost, Richardson Adventure Farm is calling. Its 2026 corn maze celebrates America’s 250th anniversary, with 28 acres of winding trails and maze games. There’s also a pumpkin patch, wagon rides, a 700-foot zip line, a 50-foot observation tower, ORBiting, live pig races, jumping pillows, giant slides, pedal carts, picnic areas and campfires. The fall season runs now through Nov. 1, 2026, with hours varying by day.

More information: Richardson Adventure Farm website 

Pumpkin festivals and fall fun closer to the city

Not in the mood to spend half the day driving? Chicago and its nearby suburbs have their own fall attractions, including pumpkin-filled street festivals, seasonal pop-ups and glowing jack-o’-lantern displays.

10. Jack’s Pumpkin Pop-Up

Goose Island, Chicago

Jack’s brings pumpkin-season festivities to Goose Island, with themed photo installations, carnival games, food vendors, axe throwing and a large corn maze. It’s an option for city dwellers who want their autumn fix without making a road trip out of it. Runs now through Nov. 1. 

11. Fall Fest at Lincoln Park Zoo

Lincoln Park, Chicago

Lincoln Park Zoo’s annual FREE Fall Fest brings seasonal decorations, a pumpkin patch, pumpkin carvers, live music and other autumn activities to the zoo. It’s a convenient choice for families who want to combine a fall celebration with a visit to one of Chicago’s familiar attractions. Runs now through Nov. 1. 

More information: Lincoln Park Zoo website 

12. The Great Highwood Pumpkin Festival

Highwood, Illinois

Highwood’s signature fall festival celebrates all things pumpkin with community carving, illuminated pumpkin displays, live music, food vendors and family activities. The glowing pumpkin walls are a particularly appealing reason to visit after dark, when the displays take on a different look. Runs Oct. 3 through Oct. 5. 

13. Night of 1,000 Jack-o’-Lanterns

Chicago Botanic Garden, Glencoe

For a different take on pumpkin season, the Chicago Botanic Garden’s nighttime event features artist-carved jack-o’-lanterns displayed along a glowing trail. It’s a seasonal outing for anyone who appreciates creative pumpkin carving and a little autumn atmosphere after sunset. Check the Garden’s event page for 2026 dates, tickets and details. Runs from Wednesday, Oct. 7- Sunday, Oct. 25. 

More information: Chicago Botanic Garden website 

14. Glass Pumpkin Patch at The Morton Arboretum

Lisle, Illinois

The Morton Arboretum’s Glass Pumpkin Patch offers a colorful alternative to the traditional pumpkin field, featuring hand-blown glass pumpkins. It’s a chance to admire the artistry, browse the displays and enjoy the Arboretum’s fall setting. Runs from Friday, Oct. 9 through Sunday, Oct. 11. 

More information: The Morton Arboretum website 

15. Apple Fest

Lincoln Square, Chicago

Lincoln Square’s annual Apple Fest brings the neighborhood together for a street festival celebrating the season, with apple-inspired treats, vendors and live music. It’s a city alternative for those who prefer strolling a neighborhood festival to wandering an orchard. Runs Oct. 2 through Oct. 4. 

More information: Lincoln Square Ravenswood Chamber of Commerce 

Before you go

A little planning can make the difference between a picture-perfect fall outing and a long drive to discover the apples have already been picked.

• Check the harvest first. Apple varieties ripen at different times, and availability can change quickly. Confirm that pick-your-own apples are available on the day you plan to visit.

• Look at admission details. Some farms charge separately for orchard access, picking bags, rides, mazes and other attractions.

• Check the weather and operating schedule. Outdoor activities may change with weather conditions, and some farms operate only on select weekdays or weekends.

• Buy tickets in advance when required. Popular seasonal events can have timed entry or advance-purchase requirements.

Fall in the Chicago area is wonderfully short, so make the most of it. Whether your ideal afternoon involves filling a basket with Honeycrisps, finding a pumpkin worthy of your front porch, getting lost in a corn maze or admiring thousands of glowing jack-o’-lanterns, there’s a seasonal adventure waiting just beyond the city limits.

(Seasonal details can change. Confirm dates, hours, ticket requirements and crop availability directly with each destination before traveling.)

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