Bust out your boots, 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 guide to Chicagoland Apple Orchards & Pumpkin Patches with updated info for 2026! I’ve also noted which produce you can find at each location with emojis. 🎃🍎🌻🍓

🍎 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 $26 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!

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 🙂

🍎🎃 Keller’s Farmstand – Oswego, IL

Keller’s Farmstand‘s main farm and festival is in Oswego. You can find donuts, pumpkins, apples, and more at the Naperville shop.

🍎🎃🌻🍓 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. Apple picking begins August 21. Their pick-your-own pumpkin patch usually opens at the end of September.

🍎🎃🌻  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! This year they have two festivals. Blooms & Bushels Festival runs Aug 22-Sep 17, 2006. This festival will include the Fall Flower Fields and the U-Pick Apple Orchrd. Fall Harvest Fest runs September 18th through November 1st and will feature the Pumpkin FunFarm and U-Pick Apples.

🍎🎃🌻 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 Orchard opens August 26, 2026!

🍎🎃 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 29. 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.

🎃 Bengtson’s Farm – Homer Glen, IL

Bengtson’s Pumpkin Farm hosts their annual Fall Fest beginning September 4th, 2026. They’ve got rides, a petting zoo, live music, pig racing, hayrides, and more!

🍎🎃 Honey Hill Orchard – Waterman, IL

Honey Hill Orchard is a family-run farm with U-Pick berries, apples, and pumpkins. 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! Opening day is September 4, 2026.

🍎🎃 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. Their fall season opens Labor Day weekend 2026.

🍎🎃🌻🍓 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 September 5 and November 1, 2026. 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.) The farm also has beets, green beans, sunflowers, and more!

🍎🎃🌻 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! Apple picking and Fall Fun begin on September 5, 2026. 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.

🍎🎃🍓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! Their u-pick is open now but Fall Festivities begin September 5, 2026.

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

Johnson’s Farm Produce has a storefront and farm market open every day. U-Pick season is coming soon! Their sunflower fields open September 12, 2026 and Pumpkin U-Pick and Fall Fest will start Sept 26. The Fun Farm looks like a blast!

🎃 Halloween in the Parks – Chicago, IL

If you want to 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. Their first fall event is on September 25!

🎃🍎🌻

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