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The Best Places To Ride Your Bike In Chicago Fall 2021

Updated On: August 11, 2021

Any time you are riding your bike it is a good day, and any time you are lucky enough to spend some time in Chicago in autumn, you can feel grateful. When you combine the two you have the makings of an epic adventure.

The Windy City, even when you take into account the challenging riding conditions in wintertime, ranks pretty high as a biking destination. It has decent bike lanes, an active biking culture and many excellent places to ride. At Sixthreezero, we believe what puts the city over the top as a place to pedal are the many top-tier attractions, the spectacular food and the energy of the city.

A couple of parks offer interesting places to ride. Millennium Park is in the thick of things and has enough paths to make for enjoyable riding in the green space as you look at the people and sculptures, including the notorious Bean (or Cloud Gate). Nearby Grant Park also is a solid option. Guided bike tours can also be fun and they have the benefit of taking you on a planned and safe route through the city.

Bike Trails & Paths In & Outside The City

While city street riding is an option, there will be times you want to take the stress out of dealing with traffic. Fortunately, you have several attractive routes on bike trails and paths. The North Branch Trail follows the North Branch of the Chicago River and it allows you 16 miles of riding, plus four more if you tack on the loop around the Skokie Lagoons. The trail takes you through some towns and forests and gives you access to the Chicago Botanic Garden.

Other excellent options wind in and around the city and are perfect for the cool weather of fall. These trails are all within a few miles of Chicago:

•      The Mayor Traylor Trail meanders past woods and neighborhoods of the far South Side

•      The Des Plaines River Trail goes for 56 miles from Elmwood Park to the Wisconsin border

•      Made of crushed limestone, the Illinois Prairie Path runs through Chicago's west suburbs

•      The Valley Line Trail snakes its way through the green spaces of the northern suburbs

No piece on Chicago biking would be complete without a mention of the Lakefront Trail. This 18-mile trail closely follows the shoreline of Lake Michigan, offering splendid views of the Great Lake and the city skyline. It can get busy in the summer, so fall is an optimal time to try it out.

The Chicago Riverwalk & The 606

If you want to be in the midst of it all, the Chicago Riverwalk has sections open for biking. This route takes you through some world-class architecture along the Chicago River, and though it is short it is packed with star power. You get to pedal under bridges and take in the action of one of the prettiest areas of the city.

An abandoned rail line, the 606 goes for 2.7 miles and has several desirable features. As you pedal you pass an observatory, parks and art installations. The pathway also connects several neighborhoods, including Wicker Park and Bucktown, and it is a great way to traverse the city from west to east.

Chicago eBike Laws & Requirements

At Sixthreezero we know that riding safely and responsibly enhances your enjoyment. If you tackle the trails on an e-bike, know that Chicago has an ordinance that allows motorized electrical bikes as long as they meet certain requirements: they must weigh less than 125 pounds, they must not be operated in full electric mode and they shouldn't exceed 20 miles an hour under electric power.

We have many bikes to help you get the most out of a Chicago bike trip. Check out Sixthreezero bikes online to see our large selection.


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