Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In

Become a Member

Get access to more than 30 brands, premium video, exclusive content, events, mapping, and more.

Already have an account? Sign In


Pennsylvania Trails

Pittsburgh, PA: South Side Steps

Climb a few of Pittsburgh's 700-plus stairways on this 3.2-mile urban loop that begins in the trendy South Side neighborhood and tops out with a skyscraper city view from a cemetery atop Mount Oliver.

Get full access to Outside Learn, our online education hub featuring in-depth fitness, nutrition, and adventure courses and more than 2,000 instructional videos when you sign up for Outside+ Sign up for Outside+ today.

This Pittsburgh neighborhood on the south side of the Monongahela River has the highest concentration of public stairways in the city—an impressive count for a city with more than 700 of them. Some of the houses you’ll pass are only accessible via stairs and the hilly terrain makes this a great workout.
Beginning on Josephine Road, this loop follows a route from the 2009 Step Trek event, a fundraiser and community building event put on by the South Side Slopes Neighborhood Association. You’ll hit the first set of steps (under the Mission Street Bridge) just a few hundred yards into the loop and continue climbing gently as the route loosely follows busy South 18th Street for the next 1.5 miles. You’ll turn left from the sidewalk into South Side Park at Quarry Fields and zig-zag up neighborhood streets, behind tall, crumbling houses. After a steep climb up Quarry Way, stick to the sidewalk –stop to admire the mural across the street—and branch left for a short detour into St. Michael’s Cemetery where you’ll get an excellent view of the city to the north.
Continue following South 18th and drop into Johno’s Art Studio before turning right on Arlington for the short uphill to this route’s high point. You’ll descend for half a mile, dipping toward another city viewpoint on Warrington Ave. and looping west of St. Paul of the Cross Monastery before climbing again up Buckingham Hill. Loop end holds the most impressive stairway, a long, curving beauty with more than 150 steps that descends from Pius Street to South 18th. Cross under the train tracks and head east on the industrial-feeling edge of the South Side back toward your car.
-Mapped by Kristy Holland


Trail Facts

  • Distance: 5.2



Location: 40.424858, -79.976038

There is plenty of parking on Josephine Street both east and west of 21st. Park and begin by waking south on 21st and looking right, for the staircase under the Mission Street Bridge.


Location: 40.421508, -79.979486

After a short walk on the sidewalk alongside S 18th Street, turn into South Side Park and follow the wide walking path to its northern border.


Location: 40.42079, -79.985023

There are several short side streets that link to South 18th Street, but the walk on Quarry Way is relatively traffic free; probably a result of the steep, steep grade.


Location: 40.418757, -79.986284

The detour into St. Michael’s Cemetery is worth a few minutes. Follow the path toward the top of the hill and look north over the impressive tombstones–some over 150 years old–toward downtown skyscrapers.


Location: 40.417613, -79.986348

There’s a local artist’s sutdio and a gas station on this busy corner. Use the traffic signal to cross South 18th and continue climbing toward the route’s high point on Arlington Avenue before turning downhill on Amanda Street in a few blocks.


Location: 40.422081, -79.986649

Look north over empty lots toward the city–another prime viewpoint–before turning right at this T-junction on Warrington Avenue.


Location: 40.423412, -79.985586

This mapped route loops down the street-side steps toward a small green-space park on busy Brosville Street and skirts this intersection again. You could cut 300 yards from this route by just turning east toward the monastery at this point.


Location: 40.424458, -79.980876

Look for this hidden right turn toward the last set of steps on this route. There’s a small war memorial less than 100 feet west and, though it’s worth the detour, if you pass it on your right, you’ve gone too far. Use the railing as you descend, it’s a long, bending and exposed staircase toward South 18th.


Location: 40.425009, -79.980976

Though you could turn right alongside this busy stretch of road and beeline toward loop-end, there isn’t a safe crossing and cars coming under the railroad tracks don’t have much visibility. Opt to cruse under the tracks and head east toward 21st Street on more pedestrian-friendly streets a few blocks north.

First Flight

Location: 40.423674, -79.976816

The steps under Mission Street are the first set on this loop.

Quarry Field

Location: 40.421505, -79.979487

Turning onto the footpath in South Side Park’s Quarry Field.

Children Playing

Location: 40.420692, -79.981166

Though this route skirts a few major roads, there isn’t much traffic on some of the smaller side streets.


Location: 40.419475, -79.987593

The steep climb up Quarry Way intersects a mural-decorated curve on South 18th Street.


Location: 40.418769, -79.985007

St. Michael’s Cemetery has tombstones dating back more than 100 years and offers a great view of the city.

Monastery Street

Location: 40.423416, -79.985576

Looking back toward St. Paul of the Cross Monastery from the steps on Monastery Street.

Step Trek Signs

Location: 40.423951, -79.985973

The annual event is in the fall and if you attempt a Step Trek route around event-day, you may still see signs dotting the route.

Billy Buck Hill

Location: 40.421883, -79.981373

A softball field and a short uphill climb up Yard Way.


Location: 40.424486, -79.981029


Location: 40.424876, -79.980852

A big, long flight of steps near the end of the loop.

How to Pack for Backcountry Skiing

Get to know the winter safety gear you need in your pack.