Sledding in the City

sledding Sledding in the City
Photo Credit: Seth Anderson

To the truly adventurous, nearly any plot of sloped land can be an ideal place to sled. However, not everyone looking for a little Winterized fun is willing to risk a cracked skull, runaway sled or a ticket for trespassing. If that sounds like you, here’s a list of some of the city’s best hills.

Caldwell Woods 6200 W. Devon Ave., just west of Milwaukee Ave.
Although you can’t use the old toboggan hills, which is a tragedy, the Caldwell Woods are still a blast. Aside from the biking and walking trails, several large slopes line Devon just waiting to be tackled. Just be careful not to crash into the dozens of deer that usually gather along the edge of the trees.

Cricket Hill Montrose Ave. and the Lake
Located at Montrose Harbor, Cricket Hill is one of the more popular sledding destinations on the north side. It scores extra points for the beautiful lakefront view and the gorgeous park around it.

Dan Ryan Woods 87th and Western Ave
The Dan Ryan Woods, located in Beverly, are one of the few places in Chicago where you can get attacked by wild dogs and hit the slopes. I kid — wild dog attacks are only a risk if you venture off-path and into the woods. The giant sledding hill would be worth the risk anyway, though. It’s that fun.

Gomper’s Park 4222 W. Foster Ave.
Gomper’s Park is definitely one of the city’s little hidden gems, though that charm isn’t directly related to its sledding hills. Located on the north end of the park just west of the field house, Gomper’s smallish hills are best suited for children or those who are absolutely terrified of sledding for some reason. That being said, the little ones will have a blast.

Schiller Woods Irving Park Rd and Cumberland Ave
Come loaded with apples — there are plenty of deer here too!

Soldier Field E. 18th Dr. at South Museum Campus Dr.
This Lakefront Trail sledding hill is especially notable for the way it wraps all of Chicago into the experience. The incredible view of the skyline from the top of the hill provides all the motivation you’ll need to keep climbing back up, not to mention that it makes for an excellent make-out spot. Hot cocoa and Eskimo kisses, anyone?

Stearns Quarry 2700 S. Halsted Ave
One of the most enchanting spots in Chicago, Stearns Quarry is home to two gigantic hills that not only offer exceptional views but seem tailor-made for some sledding action. Really, how many people can say that they’ve been sledding on a landfill?

Warren Park 6601 N. Western Ave
Warren Park offers the Rockwellian double-whammy of an outdoor ice rink and a nice sledding hill. Jack Frost himself would be hard-pressed to find a more cost-effective way to spend a winter day.



Got a favorite spot that didn’t show up on this list? Feel free to comment below and let us know about it!

Gene Wagendorf III

About Gene Wagendorf III

Gene is a writer who has spent his entire quarter century of life as a resident of Chicago. When not exploring the city he can be found wandering flea markets and garage sales or having a cigarette between classes at Northeastern Illinois University, where he hopes to acquire a degree in the next quarter century. His favorite smells are old books and bowling alleys. His poetry (how embarrassing!) can be found in issues of Kill Poet, Ditch, Word Riot, O Sweet Flowery Roses and Vowel Movements.

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