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Just got out for first ride the other night. Lakefront trail from Edgewater to North Ave. it's nice now that they separated it into 2 different paths (bike vs. pedestrian).
Here's to hoping everyone stays on the right path moving forward.
Check out AllTrails.com. Helped me a lot in finding 25+ mile mile routes in the Chicago area. Lakefront is fine but gets boring after a while!
606 but it’s not super long
Busse Woods has 12 miles of wooded trails. Des Plaines Trail is 27 miles and continues north for another 30ish into lake county.
North Branch Trail might be the easiest to get to from the city though. 30+ miles
North branch and north shore channel trail are great. 606 nice as well but it’s short and can be crowded.