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 are 15 of my favorite Midwest Pumpkin Patches and Apple Orchards for 2023! 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 sixth year and it’s truly an Instagram dream. Much less an orchard, but they do have pumpkins to purchase and take lots of pics. 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. This year the event runs from September 21 through November 5, 2023.

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 really 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 different varieties of apples, peaches, and pears. You could spend so much time here. In addition to apple picking, Apple Holler has a children’s park, farm store, and a restaurant! The Farm Park is open 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 (plus it’s cheaper on weekdays), but later in the season shouldn’t be too crowded. Plus, it’s not too far from the Mar’s 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 opens at the end of September for their 2023 season. 

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

Stade’s Farm & Market is massive! Located in McHenry County, they have their annual fall festival beginning on Saturday, September 2, 2023, through Sunday, October 29, 2023. 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 definitely 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. 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 2023 Fall Festival runs September 9 through October 30.

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 runs on weekends through October 29, 2023.

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 16 through October 29, 2023.

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. As of this writing, they have so much available for picking like green beans, cauliflower, peppers, raspberries, watermelon, and sunflowers! Brussel sprouts, gourds, and pumpkins are coming soon.

Johnson’s has a Pumpkin Festival running weekends from September 23-October 29. General Admission includes all the fun farm activities except the train and produce cannons. 
We went the summer after COVID lockdown 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 every year. They have some of the best cider donuts! It’s not super big and does get really crowded. We really 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 is open daily from August 30 through October 31, 2023.

12. 🎃🍎 Garwood Orchards – La Porte, IN 

I actually haven’t been to Garwood Orchards, but it is FIRST on our list this fall. A friend told me about it and raved 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.

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! Be sure to also check out my fall bucket list and eight unique date nights to do this fall! 

Christine