4 Pick-Your-Own Wisconsin Apple Orchards Near Chicago

Escape to a place where you can experience autumn’s beauty and enjoy the fall harvest with your favorite people. All of these apple orchards are less than a two-hour drive from Chicago, and also are easy pickings for Madison and Milwaukee folks. Trade skylines for treelines for a day (or weekend!) and bring home some delicious treats, too.

Apple Barn Orchard and Winery – Elkhorn

How about some sweet fruit wine with your apple haul? Head to the Apple Barn for free seasonal tastings. They use a plethora of different juices in their award-winning wines, including apple raspberry, rhubarb, cranberry and more. Choose from more than a dozen varieties of apples to pick with friends and family, along with seasonal strawberries and pumpkins. Have a warm apple cider donut (or three) in the fresh fall air for the perfect autumn adventure.

Apple Holler – Sturtevant

You’ll get the full Wisconsin experience at Apple Holler, a former dairy farm which now houses a 70-acre orchard, restaurant, Kids Koral and Farm Park. Take a hayride and pick your own apples, pears, peaches, pumpkins and sugar snap peas before browsing the Country Store for tasty baked goods and gifts. Then, enjoy a hearty meal and crisp cider in the biergarten together with a view of the orchard. And don’t forget to take a homemade pie home to commemorate your trip.

The Orchard Store at Old Homestead – Caledonia

It’s all about the history at Old Homestead Orchard. The Drought family has owned the land since 1840, and today’s fruit farm grew from the family’s original small orchards. After you’ve picked your fill of apples and sunflowers, take time to browse the vintage and antique shop. Then, share some one-of-a-kind treats together like apple “nachos” with caramel sauce, homemade honey lemonade and apple cinnamon brats.

Bring the whole family to opening weekend Honey Fest the first weekend in September to sample one-of-a-kind honey varieties like cranberry blossom and bourbon barrel!

The Elegant Farmer – Mukwonago

The Elegant Farmer is home to the Gourmet Apple Pie Baked in a Paper Bag – named the best pie in America by the Food Network, Gourmet Magazine and the Wall Street Journal. Find more treats or lunch at the bakery or deli – from popcorn and fruit breads to cider baked ham and fresh brats – after picking your own apples with family. Visit on weekends in September and October to enjoy fall color views from hayrides and pony rides the kids will love. Then, come back in the spring for seeds, plants, flowers and small fruit trees from the garden center.

Bonus: Brightonwoods Orchard – Burlington

Located on a scenic Rustic Road between Chicago and Milwaukee, Brightonwoods Orchard is perfect for spending a fall day in nature with people you love. Right next to the Richard J. Bong State Recreation Area, both properties offer miles of trails that light up with color every fall. While this orchard does not offer pick-your-own apples, they do have a store with many fresh varieties as well as cider, local Wisconsin cheese, maple syrup and more.

Want to stay a while in Wisconsin? Check out these cabin rentals close to Chicago to keep the fun going even longer!