2 hrs from Chicago, 11K apple trees, pumpkin patch. $10 dog admission, leashed at all times.
Visit Appleberry Farm in Cross Plains, WI for caramel apples, cider, and donuts. U-pick apples, dog-friendly weekend in Madison.
U-pick farms in Belleville, Grafton, Millstadt. Apples, fields pass required. Leashed dogs welcome (except berry/veggie fields). Versailles: service animals only.
Family-owned, no-frills orchard near Elmwood. Apple picking, pumpkins, donuts, corn, mums, and more. 8am-8pm Mon-Sat. 3-hr drive from Chicago.
U-pick apples, corn maze, cider house. Howl-O-Weekend in Oct. Dog-friendly once a year.