Family Friendly Fall-Inspired Farm Festivities in Illinois and Wisconsin

Oct 11, 2025

There’s nothing better than crunching into a freshly picked crisp, juicy apple right from the farm! And it’s even better if you’ve spent the day celebrating all things fall with your family. Each of the farms highlighted on today’s list brings a unique Fall Festival or Autumnal Celebration to enjoy with your loved ones, as well as unique treats such as heirloom apples, signature cider donuts, and more. You’ll find the perfect fall destination that’s absolutely worth taking a road trip in your new car from Classic in Waukegan. We know you’re going to have a blast picking fresh apples, the perfect pumpkin, and sampling those homemade baked goods. Of course, if you also saw it fit to bring your friendly neighborhood car dealer a few cider donuts to share, we surely wouldn’t complain! So, hop in your car and let’s hit the dusty farm road for some classic family-friendly fall festivities on today’s blog.

Richardson Adventure Farm in Spring Grove is a great family-friendly destination for fall fun. There are more than 30 different activities to enjoy on the farm year round, but autumn activities are where it’s at. This fall you can enjoy the World’s Largest and Most Intricate Corn Maze featuring 28 acres of live corn and 9-10 miles of walking, the Pumpkin Patch and Sunflower Field, community campfires, and more. Pumpkins are available to pick your own, and come in a variety of shapes, sizes, and colors! This year’s corn maze theme is Back to 1985 and celebrates the iconic Back to the Future franchise!

Goebbert’s Farm in South Barrington is hosting its annual Fall Festival now through October 31st. Highlights of this year’s festival include the Pumpkin Eating Dinosaur, Cornstalk Maze, a Haunted House, Charlotte’s Web play area, the Corn Box playground, and even Pig Racing! The Harvest Market is also open daily, and will have a selection of pumpkins, fall decor, fresh veggies, and baked goods to enjoy! We highly recommend checking out the apple cider donuts, they’re to die for.

Sonny Acres Farm in West Chicago is hosting their annual Fall Festival from now through October 30th. Families can enjoy pumpkin picking, classic hayrides, fall themed food, games and amusements, and much more. Plus, as a spooky Halloween celebration, there are two Terror-iffic attractions to choose from: Wicked Hallows Hayride, bringing you through cursed forests and farm, and the Haunted Barn: Curse of the Scarecrow scare challenge and haunt! You’ll need tickets in advance for those and they’re filling up quickly, so don’t miss out!

Kuipers Farm in Maple Park offers three different fall themed events: the Sunflower Festival, Pumpkin FunFarm and U-Pic Apple Orchard. The Pumpkin FunFarm offers numerous games, attractions, and photo opportunities for families to have some good ol’ fashioned fun on the farm. Enjoy a pumpkin themed obstacle course, games and live music, pig racing, pumpkin picking, and more! Pick your own apples in the orchard and select from a variety of in-season apples to snack on and take home for pies and autumnal baking.

All Seasons Orchard in Woodstock has been named one of the top orchards in McHenry County by USA Today and local groups! This year’s family fall fun includes multi-pack passes and ticket packages allowing you to take advantage of all the fun the farm has to offer! Enjoy 30+ attractions, apple picking, barnyard visits and hayrides, obstacle courses and games, a corn maze, ropes course, and so much more! Plus, there’s the delectable seasonal snacks including hand-dipped caramel apples, kettle corn, cider, and more.

Stade’s Farm in McHenry offers a wide selection of seasonal U-Pick options which currently includes apples, raspberries, tomatoes, peppers, green beans, and more. The Farmtractions Theme Park and Fall Festival is open on Fridays, Saturdays, and Sundays. Enjoy the Express Train, Apple Cannon, Farmtraction park and more during their special event. The “Shades of Autumn” festival is a family-friendly event celebrating the magic of the season.

Apple Holler in Sturtevant, Wisconsin offers a Family Fun Park each year from May through November! Enjoy a plethora of special seasonal activities and games, as well as agricultural education through play. This autumn you can enjoy their Apple Picking Festival featuring tractor rides, corn mazes, fall themed games, Straw Mountain the Corn Palace Corn Box, and much more. There are also several fun photo-ops this year including Giant Butterfly Wings, the Red Truck Photo Op, and the Rockinghorse Corral. The Red Barn Restaurant offers first-come, first-served seating with a seasonal menu; this month, the farm is featuring its Apple Season Menu, with applewood smoked meats, apple glazed seasoning, apple butter dips, and more.

Apple Barn Orchard and Winery in Elkhorn is in prime Apple Picking season! There are more than 4,000 apple trees in this orchard with 12 different varieties! The bakery and country store on site make fresh baked pies and cider donuts as well as fruit wines made on premise. The orchard’s social media will always keep you updated on what’s currently available for picking, and they’ve just announced that pumpkins are finally ready. The orchard and winery grounds offer multiple events throughout each season such as the Corks and Colors event, Food Truck weekends, Fall Bucket List Weekends, and more – each featuring local food, special beverages, live music and entertainment, and more.

Eplegaarden in Fitchburg, Wisconsin offers more than 100 acres of fall family fun. You can enjoy their pick-your-own fall wildflower fields, apple picking, pumpkin picking, and more. There’s a charming kids’ play area, a down home country farm store offering seasonal favorites, seasonal hayrides, and more. One of the most unique qualities about this farm is that they offer Heirloom and Antique Apples, varieties of apples that are historically favored for special practices like cider making, pipes, and more; these unique apples don’t always have a high-yield year, so they may be in limited supply, but it’s certainly worth the visit to try and catch these unique flavor varieties.

Don’t see your favorite farm on the list? Let us know in the comments section what your family’s favorite farm is in Illinois and Wisconsin, and we may just feature it in a future update!