Yeah, Yeah – we know – there are no “real” hills in the Midwest. That doesn’t mean there isn’t anywhere good to longboard around Chicago! We’ve done our research gotten feedback from all over the internets and have compiled what we have found to be a list of the best spots for longboarding in and around the Chicagoland area. Know of some great spots that we missed? Please feel free to contact us so we can add your local spot to the list.
Keep in mind, this list can’t go on forever, so we’ve tried to narrow down our favorites so you and your crew can hit the pavement and have some fun. We’ve attached links to maps and photos when we can so you can get an idea of exactly where these spots are located. Keep in mind some of these spots are more protected from traffic than others and we ALWAYS recommend using common sense when checking out new spots. Helmets are a must and slide gloves are definitely recommended. A traffic lookout or two is always a good idea also.
Without further ado, here are some of the best spots to longboard around Chicago!
18.5 miles of beautiful pathway right next to Lake Michigan. Mostly flat ground pushing but a few dips here and there. Super scenic and a great way to kill a few hours. Be sure to obey the traffic patterns because you WILL get run over by a cyclist if you drift into the wrong lane.
Chicago’s very own longboard skatepark of sorts is located right in the heart of Museum Campus – near Soldier Field. Several rolling pathways, some bigger than others, and a great place to teach yourself how to slide!
Another solid “bike” path that is also a great place to cruise. Super mellow meaning it’s never too busy, wide path for extra room and almost 10 miles long.
Running alongside the Metra train tracks on the North Shore, the Green Bay Road trail is almost 9 miles long and goes from Highland Park to Wilmette. Since the trail follows the Metra line you can even ride the train back to your starting point if you only feel like doing a one-way adventure.
A good chunk of this trail was just recently repaved (early 2016) making it super smooth and perfect for an afternoon of cruising! The full distance of the trail is just under 7 miles long and stretches from Evanston down into the northside of the city in the Albany Park / Ravenswood area. Some of the trail does still have some gravel spots but for the majority of it, you’ve got a smooth pathway.
This park is pretty cool – it has an old reservoir that is empty (which also doubles as a spot to skate) and a long path around the outside of the park. The path is super mellow with a few turns and rolling small hills and if you want to kill an extra few hours, it also has a frisbee golf course!
This residential area houses a sweet little hill on Hillcrest Drive. It’s slightly protected from traffic since it’s residential and the street is a decent width if you did have to get around a car. The best part is, the street slopes up slightly at either end so you can almost cruise it back and forth if you get enough speed going. Perfect spot to work on your slides!
Have you been to these spots and want to leave some feedback? Or want us to add your favorite spot? Let us know in the comments below and we will be happy to update our list!
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