Put on your boots and bust out the basic girl, it’s Autumn in Chicago! It’s a family tradition of ours to visit an apple orchard and a pumpkin patch in September and October every year (or at least try…) Here’s my roundup of 15 Pumpkin Patches and Apple Orchards near Chicago with updated info for 2024! I’ve also noted which produce you can find at each location with emojis. 🎃🍎🌻🙂

1. 🎃 Jack’s Pumpkin Pop-up – Chicago, IL

Jack’s Pumpkin Pop Up returns for its seventh year and it’s truly an Instagram dream. It’s much less an orchard, but they have pumpkins to purchase and plenty of great photo ops. Jack’s has a wide range of activities like “Chicago’s Largest Corn Maze,” axe throwing, tons of photo ops, carnival games, a pumpkin garden to select your perfect pumpkin to take home, and more. Kids are allowed before a certain time, check the website for that info. Dates haven’t been released yet but the website says they’ll be here in September!

2. 🎃 Halloween in the Parks – Chicago, IL

If you don’t want to drive far and stay in the city, the Chicago Park District does a great job setting up Halloween pop-ups and small patches for the kids. We’ve done a few and they are great! Our favorite was at Oriole Park. It’s free to enter but the extra things like the petting zoo, hay rides, etc. are all ticketed. You can find a full list of parks doing their fall celebrations here!

3. 🍎 Apple Holler – Sturtevant, WI 

Apple Holler is about 65 miles from Chicago and it’s a fan favorite for a reason! The orchard is 78 acres with over 50 varieties of apples, peaches, and pears. You could spend so much time here. Entry into the orchard is $22 per person this year but that includes so much! In addition to apple picking, Apple Holler has a children’s park, farm store, and a restaurant! The Farm Park is open June through November and includes play structures, feeding goats, a giant slide, and Pedal Karts.

This is an orchard I would probably only go to during the week, but later in the season shouldn’t be too crowded. Plus, it’s not too far from the Mars Cheese Castle, so you can get your apples and cheese all in one day 🙂

4. 🍎🎃 Royal Oak Farm Orchard – Harvard, IL

Royal Oak Farm Orchard, near the Wisconsin border, has 160 acres of farmland and four different orchards. The property contains an apple tree maze,  playground, petting zoo, train rides, a carousel, stores, and a bakery. Their pick-your-own pumpkin patch usually opens at the end of September.

5. 🍎🎃 Stade’s Farm and Market – McHenry, IL

Stade’s Farm & Market is massive! Located in McHenry County, they have their annual fall festival every weekend between August 31 and October 27, 2024. It’s sort of like a Farm and amusement park all in one. There’s a small Ferris wheel, zip lining, slide mountain, and more. You can spend all day here! I love that general admission includes parking and almost all the attractions. (Shooting apples out of cannons costs extra.)

6. 🍎🎃 All Seasons Orchard – Woodstock, IL

All Seasons Orchard, also in McHenry County, has U-Pick apples and pumpkins and a whole Fun Farm to explore. Opening day is August 31. This one does get fairly crowded on the weekends, but it’s so fun for the kids! They have lots of family-friendly activities, even having a magician last time we were there! I would recommend going early and during off-peak times.

7. 🎃 Goebbert’s Farm & Garden Center – South Barrington, IL

I love, love Goebbert’s Farm Fall Festival! We have gone for the past few years. There’s a lot to do, the market is really cute, there are hay rides and a corn maze, and they have a wide range of activities for various ages (the bouncing pillow is great for 7-10-year-olds). You can buy tickets in advance, and I highly recommend it so you don’t have to wait in line. It does get crowded, but we have always gone right when they opened. It’s definitely an all-day type of thing! Their 2024 Fall Festival runs from September 7 through October 31.

8. 🍎🎃 Jonamac Orchard – Malta, IL

Jonamac Orchard is about an hour or so outside of the city and it’s a big apple orchard and farm! They even had wine tastings the last time we were there! It’s not far from St. Charles so you can make a day out of it and stop by for dinner in downtown St.Charles on your way out. Their 12-acre U-pick pumpkin patch opens in mid to late September. You can also buy pre-picked pumpkins in their Pumpkin Barn behind the store and bakery. Jonamac’s Fall Festival begins August 21, 2024.

9. 🍎🎃🌻  Kuipers Family Farm – Maple Park, IL 

Kuipers Family Farm is probably one of the more popular apple orchards in the Chicagoland area and I find it gets really, really crowded! It’s very nicely laid out and there is a lot to do, but I would recommend going during off-peak times! They have u-Pick Apples, a Sunflower Field for photo ops, and a 50-acre Fall Festival “FunFarm” running September through November 3, 2024.

10.  🎃🌻🍓 Johnson’s Farm Produce – Hobart, IN

Johnson’s Farm Produce has a storefront and farm market open every day and all their u-pick fields are open on Saturdays and Sundays.

Johnson’s has a Pumpkin Festival running weekends from September 28-October 27. General Admission includes all the fun farm activities except the train and produce cannons. 

We went in the summer of 2020 to get some fresh air and LOVED it! The kids were able to pick so many blueberries and other fruits and vegetables. There’s a cute market and kid’s playground on the grounds. They also have a pretty active IG to stay updated on all the events they have throughout the fall!

11. 🍎🎃🌻 County Line Orchard – Hobart, IN

I have been going to County Line Orchard for years now! I used to take my students when I was a teacher. They have some of the best cider donuts! It’s not super big and does get crowded. We like it because it’s not too far from the city. They have u-pick sunflowers, apples, and pumpkins, and lots of other kid-friendly activities. My suggestion would be to go super early and even on an off day. County Line’s season begins on August 28, 2024.

12. 🍎🎃 Garwood Orchards – La Porte, IN 

I haven’t been to Garwood Orchards, but it’s FIRST on our list this fall after a friend came back raving about it. The reviews all look great too! It’s been around since 1831, so they must know what they are doing. Their September U-Pick includes apples, pumpkins, hot peppers, blackberries, and raspberries!

13. 🍎🎃 Crane’s U-Pick – Fennville, MI

Located right outside Saugatuck (check my family Saugatuck post for more!), Crane’s U-Pick might be our favorite. First, it’s huge! There’s so much to do, you could spend all day here. Bakery on site, a corn maze, hay rides, games for the kids, a general store, and obviously, apple picking. This is one of the further apple orchards, so this might be more of a weekend thing. But we love the area and there’s a lot to do with families and for the adults.

14. 🍎🎃 Honey Hill Orchard – Waterman, IL

Honey Hill Orchard is a family-run farm with U-Pick berries, apples, and pumpkins. Their fall season is every weekend between September 7-October 27. They’ll have wagon rides, a children’s play area with a petting zoo, fresh baked goods and gifts, and food trucks most weekends, too!

15. 🍎🎃 Keller’s Farmstand – Oswego, Naperville, and Plainfield, IL

Keller’s Farmstand‘s main farm and festival is in Oswego and opening day is Saturday, September 7. You can find donuts, pumpkins, apples, and more at the Naperville and Plainfield shops.

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OK, Chicago! I hope you find your favorite pumpkin patch or orchard this year! If you go to any of these, tag me in your Instagram photos and stories! You can find more fall content here!

Christine