Father and son sledding down hill

Where to Go Sledding in Milwaukee: 12 Great Hills and Parks

Winter is here, and Milwaukee has a number of terrific sledding hills for you and your family to go whipping down (and then trudging back up).

Once the cold weather hits, it’s way too easy to spend the weekends and evenings in front of the TV with a (preferably spiked) mug of hot cider. Thus, it’s important to bring back some of that childlike elation at the sight of snowflakes — especially if you have kids of your own cooped up inside! While you could strap on skis or ice skates, the most readily available path towards exhilarating fun is to grab a flimsy piece of molded plastic and head for the hills. And luckily, in Milwaukee, there’s no shortage of sledding spots to go hurtling down.

Here’s a handful of designated safe places to drag your toboggan to, adapted from a list made by the county. Just don’t forget the snow pants and ski mask — warmth always takes precedence over fashion after a few minutes in freezing weather.

Daytime Sledding Hills

Columbus Park, 7301 W. Courtland Ave. (West Side)

This 385-acre park boasts one large sledding hill as well as gentler rolling hills, making it perfect for children of all ages. Plus, with its forest trails and open spaces, Columbus Park feels like you’re “up north” instead of in the city — that is, if “up north” had public restrooms.

Hawthorn Glen, 1130 N. 60th St. (North Side)

This quiet park is focused on preserving nature and is generally less frequented than other nearby parks. Therefore, while the sledding hill here isn’t the steepest you’ll find in the city, it’s a good choice if you’re looking for a bit of freedom from the crowds. 

Kilbourn Reservoir Park, N. Bremen St. (Riverwest)

What Kilbourn lacks in space it makes up for in altitude. Boasting some of the best views of the city, you’ll get some serious air at this step-hilled spot in Riverwest — just make sure to plan your path with the surrounding streets in mind so you don’t end up with a little less fun than you bargained for.

LaFollette Park, 9418 W. Washington St. (West Allis)

If LaFollette Park was a ski resort, it’d just be one giant bunny hill. While you’ll spend a lot of time walking back up after a ride, a long but less steep incline makes this sledding spot perfect for little ones who are still getting used to staying on the sled.

McCarty Park, 8214 W. Cleveland Ave. (West Side)

With small rolling hills, McCarty is another good option for the non-thrill-seeking sledder. Additionally, the Oak Leaf trail runs through the park, making it a great place to stroll under the snow-covered trees on a non-bitterly cold day.

St. Mary’s Hill, 2323 N. Lake Dr. (East Side)

With a steep incline and beautiful views of the lake, St. Mary’s is one of the best sledding spots in the city. Just keep safety in mind as this hill’s final destination is a parking lot. Hay bales may prevent sleds from drifting too far, but this site is still best for the experienced sledder.

Wilson Recreation, 4001 S. 20th St. (South Side)

For the family that enjoys a variety of wintertime activities, Wilson Recreation should be at the top of your list. While you could spend all afternoon gliding down the packed snow, check the center’s website ahead of time to coordinate your sledding plans with the hours for open admission to the indoor skating rink.

Lighted Sledding Hills (for night sledding from 4:30 p.m. onwards)

Brown Deer Park, 7835 N. Green Bay Rd. (Brown Deer)
lit until 8 p.m.

The sledding hill at Brown Deer is short compared to others; however, the drop is not for the faint of heart. Likely due to the rush of adrenaline, evening hours and beautiful location, this hill can quickly become overcrowded — try to make it out early if you can!

Currie Park, 3535 N. Mayfair Rd. (Wauwatosa)
lit until 9 p.m.

The main hill here isn’t particularly steep. But what it lacks in speed it makes up for with space: little ones aren’t at risk for veering into the pines here. Also, seeing as this park also features a massive dog park and an indoor (heated!) snack bar near the golf course, this may be the place to come if you’re looking to spend the whole day in the snow.

Humboldt Park, 3000 S. Howell Ave. (Bay View)
lit until 8 p.m.

While this beloved neighborhood park doesn’t boast big drops, it is a perfect place to relax and enjoy the company of other happy Bay Viewers. With an abundance of lights, you can also sled well past sunset. Still, the best feature of Humboldt Park may be its location — sledders can choose from a number of nearby trendy restaurants or bars to warm up in afterwards.

Pulaski Park, 2677 S. 16th St. (South Side)
lit until 10 p.m.

A little less known than other parks, this is a great place to come if you’re aiming to go flying over some powdery snow. Additionally, you won’t have to pack up your sleds, saucers or toboggans once the sun goes down — most of the hills here are lit up at night.

Whitnall Park, 5879 S. 92nd St. (Franklin)
lit until 10 p.m.

This uber-steep (albeit sometimes icy) sledding hill is cozied up next to a toboggan run, making Whitnall the go-to place for serious sledders. Whitnall also features a clubhouse where snow fiends can kick back, grab a snack and even indulge in a local Wisconsin ale after a long day in the cold.