Chicago’s Most Amazing Bike Trails

words Al Woods

Chicago Bike Trails

Chicago is one of the most bicycle-friendly cities in the United States, so if you live in the Windy City or are visiting, you’ll have plenty of trails to ride along.

There are multiple bike trails that offer beautiful landscapes and amazing sites along the way. 

Here’s our pick of the best.

North Branch Trail

This trail is nearly sixteen miles long but it also includes a four-mile loop, so it’s ideal for short bicycle rides or a full day of exploration.

The North Branch Trail starts at Gompers Park and continues northwards to the stunning Skokie Lagoons, running alongside the Chicago River.

There’s a paved section of the trail, which winds through the forests of Nile, Skokie, Morton Grove and Winnetka.

At the end of the trip, you’ll be near Chicago Botanic Garden, which is a beautiful and relaxing site to rest after your journey.

Major Taylor Trail

Some trails are made just for bikes, and perhaps skateboarders and people on rollerblades; such as the paved section of the North Branch Trail. But others, like the Major Taylor Trail, share the road with cars.

Of course, when multiple vehicles use the same road, accidents are more likely to occur, so make sure you take extra caution when riding on roads with motor vehicles.

If you are involved in an accident that isn’t your fault, you have the opportunity to pursue compensation with the help of a bicycle accident lawyer, but by maintaining caution, you can avoid being injured in the first place.

The Major Taylor Trail, which is over seven and a half miles long, is named after the record-breaking cyclist Marshall “Major” Taylor, who competed in cycling competitions in the late 1800s.

This trail winds through stunning forests and parks as well as the neighbourhoods on Chicago’s Far South Side.

The bike trail begins at Dan Ryan Woods at 81st Street and ends at the Whistler Woods Forest Preserve.

Green Bay Trail

The Green Bay Trail is almost nine miles long.

Riding along the trail is a superb way of exploring the North Shore. Beginning at Wilmette’s Village Hall, you’ll ride through Ravinia Park and several country clubs before ending up at Chicago Botanic Garden.

Most of the Green Bay Trail is paved, but there are sections that go onto roads that are shared with motor vehicles.

Lakefront Trail

If you’re looking for a beautiful trail that offers a whole day of adventure, ride along the Lakefront Trail, which runs for eighteen and a half miles from Hollywood Avenue on the North Side to 71st Street in the south.

This trail, as you may have guessed by the name, runs alongside Lake Michigan.

The best part of the trail is arguably the south shore portion, as it’s much quieter and it has some amazing views of the Chicago skyline.

North Shore Channel Trail

This paved seven-mile trail follows the North Branch of the Chicago River, beginning at River Park and ending at Green Bay Road.

During your ride, you will ride along Lincoln Village Pedestrian Bridge and pass through Legion Park, the pretty restaurants around Lincolnwood town, and the public artwork on display at the Skokie Northshore Sculpture Park.

Des Plaines River Trail

If you’re looking for a long bike trail, try tackling the fifty-six-mile-long Des Plaines River Trail, which stretches along the Wisconsin border.

Following the river, from Elmwood Park to Russell, you will wind through the gorgeous landscapes of Gurnee Woods Forest Preserve, Adler Memorial Park, and the Ryerson Conservation Area.

And if you want to break up this long trip, there are various nice places to stay along the way.

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