South Side Fall Foliage Rides

Your guide to the best fall rides in Chicago.

Now that the leaves are changing, it’s time to take advantage of the short time Chicago has to enjoy the beautiful autumn colors throughout our amazing parks! We recommend grabbing an Explorer Pass (unlimited 3-hour rides for 24 hours) and a few friends and taking this route:

Begin your journey with an amazing view of Lake Michigan and some incredible autumn colored trees at Promontory Point. Once a landfill and now a man-made peninsula, this is a hotspot for photos during an season, exercise enthusiasts, and weddings.

Divvy Station: Shore Dr. & 55th

Head south on the Lake Shore Drive path, going through the underpass at 59th St. and you’ll arrive into Jackson Park. This is over 500 acres that includes amazing things like the Museum of Science & Industry, vegetable and flower gardens and a Japanese styled garden, the Garden of the Phoenix. There’s plenty of foliage to cruise around to see and take amazing photos of in Jackson Park.

Divvy Stations: 63rd St. Beach; South Shore Dr. & 67th; Jefferson Blvd. & 67th; Stony Island Ave. & 67th; Stony Island Ave. & 64th

Finally, depending on where you are in Jackson Park, head over to 59th St. and go west into University of Chicago and their Midway Plaisance Park. It’s an incredible way to see the universities beautiful buildings and its grounds, especially with the crispness of fall as you’re biking along!

Divvy Stations: Harper Ave. & 59th St.; Ellis Ave. & 60th; Ellis Ave. & 58th; Ellis Ave. & 55th; University Ave. & 57th

Once you’re done going through Plaisance Park it’s time for a meal from a place that’s been serving up amazing food in Hyde Park for over 55 years! Park your bike at University Ave & 57th, walk a couple of blocks east, and you’ll arrive a Medici on 57th. Originally a coffee house back in 1962, this staple of the neighborhood now is baking amazing things and can crank out incredible pizzas!

Divvy Station: University Ave & 57th

Want to keep riding? Check out our West side route.

Divvy is great for short rides too such as running errands and getting to work. Grab your Explorer pass and get going today!

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