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The Best Fall Festivities as leaves turn orange

Posted on October 4, 2022   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

City Cast's Carrie Shepard smiling and grabbing an apple from a tree

City Cast's Carrie Shepherd at Edward's Apple Orchard in Poplar Grove. (Provided)

llinois and the Midwest are really magical this time of year, with the leaves changing colors and beautiful sunsets. Here are some ways to take in the season:

Apples always taste a little sweeter when you pick your own, yeah? Edward’s Apple Orchard was where I went growing up, but you don’t have to go all the way to the northern border. There are some apple picking places closer to the city.

You can also stay close to home for your yearly pumpkin picking. Jack’s Pumpkin Pop-Up in West Town brings the farm to you! Plus, axe throwing, a corn maze and food trucks!

Take in the scenic views along the Mighty Mississippi with an itinerary that includes hot air balloons, wineries, hiking, and more from the Illinois tourism office.

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