Escape across the border to a place where you can experience autumn’s beauty and even reap the fall harvest for yourself. All of these apple orchards are less than a two-hour drive out of Chicago, and also are easy pickings for Madison and Milwaukee folks. Get out of the big city and into Wisconsin’s colorful countryside!

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, pear, peach, wild blackberry, mulberry, raspberry, cherry, rhubarb, blueberry, cranberry and even pumpkin. Choose from more than a dozen varieties of apples, along with seasonal strawberries, peaches and pumpkins. Have a warm donut and cider, and don’t miss the tractor-train rides!  

Apple Holler – Sturtevant

You’ll get the full Wisconsin experience at this former working dairy farm, which houses a 70-acre orchard, restaurant, store and lunch/dinner theater. Take a hayride and pick your own apples, pears, peaches, pumpkins and sugar snap peas before browsing the Country Store for baked goods, deli items and gifts, then enjoy a hearty, down-on-the farm meal. Check the calendar of events before you visit to catch farm tours and even trips to shows in Chicago!

The Orchard Store at Old Homestead – Caledonia

It’s all about the history at Old Homestead Orchard. The Drought family has owned this Racine County parcel since its purchase from the government in 1840, and today’s fruit farm grew from the family’s original small orchards. After you’ve picked your fill of apples, pears and raspberries, take time to browse the vintage and antique shop. Droughtville Farms, the family’s homestead, also sells raw honey, fresh eggs and naturally raised poultry.

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 – and they ship to customers all over the U.S. Find a treat or lunch at the bakery or deli – from popcorn and fruit breads to cider baked ham and fresh brats – after picking your own apples, pumpkins and squash. Come back in the spring for seeds, plants, flowers and small fruit trees from the garden center.

Want to stay a while in Wisconsin? Check out more outdoor adventures and cabin rentals close to Chicago to keep the fun going!