Seven places to sled within the city of Pittsburgh | Winter Guide 2021 | Pittsburgh | Pittsburgh City Paper

Seven places to sled within the city of Pittsburgh

click to enlarge News Editor Ryan Deto sledding down Flagstaff Hill - CP PHOTO COLLAGE
CP photo collage
News Editor Ryan Deto sledding down Flagstaff Hill
Hills proliferate so much in the region, that even the city of Pittsburgh has several places for some premium sledding. No need to leave the city to enjoy a snowy day sliding down the hill. For a lot of residents, there's no need to even get in a car. Just grab your saucer, sled, or toboggan, and walk to the nearest slope. Here are seven great hills for all the urban sledding enthusiasts living in Pittsburgh.

Flagstaff Hill

Across the street from Phipps Conservatory in Schenley Park, Oakland
On warmer nights, this popular hill is usually full of students hanging out, but in the winter, it’s wide open for some seriously epic sledding. Enter the hill from Schenley Drive or through Carnegie Mellon University’s campus. (Please be careful – if you pick up too much momentum, you might end up on the road.)

Observatory Hill

Located in front of the Allegheny Observatory in Riverview Park, North Side
Another epic hill used in the summer for concerts and movie screenings. Hike to the top, just in front of the Allegheny Observatory. On a clear day, you might be able to spot Pittsburgh’s three rivers through the barren trees, just before you sled down this large hill in the North Side.


The hill near Blue Slide Park

Across from the Blue Slide Playground in Frick Park, Squirrel Hill
This is one of the safest hills, as there is no chance of sliding into the street. Start up near the sidewalk entrance to Frick Park, near the Blue Slide Playground. (This one is easy to find and is tagged on Google Maps.) Slide to your heart’s content. Just make sure to stop before sledding into the woods.

Chapel Hill

Intersection of Woodland Road and Chapel Hill Drive on Chatham University campus, Shadyside
Located in the heart of Chatham’s campus, Chapel Hill is more difficult to find compared to other locations on this list but is worth the trip if you are looking for a more secluded hill. Start from the top of Chapel Hill Drive, and slide down on a gentle slope.

Cowboy Hill

Near the end of S. Dunfermline Street in Frick Park, Point Breeze
Another hill in the less-visited area of Frick Park, Cowboy Hill is accessible with a short hike on Hawthorne Trail (start at the end of S. Dunfermline Street). Sled in seclusion, surrounded by trees and woods from all sides.

Mellon Park Hill

Near the Phipps Garden Center in the South section of Mellon Park, Squirrel Hill
A small, but secluded hill located near the Squirrel Hill and Shadyside border in Mellon Park. If you are feeling adventurous, you can start your sled from the very top and dodge some trees along the way.


Hill near Gardens of King Estate

Located on the other side of the street from 5591 Elgin St., Highland Park
Highland Park is loaded with hills for sledding, and this is a good option near the edge of the neighborhood. Not too large, but far enough away from the busy thoroughfare of Negley Avenue.

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