South Side Park reaches farther down the hill than most people picture. When the Pittsburgh City Planning Commission approved the park in 1948, its plan joined the Sophia Everet Playground and the Arlington Playground with the land between them, "crossing Mission Street and ending near Josephine Street." That puts the bottom edge of a 65-acre wooded valley down on the Flats' own street grid.
That bottom edge is also the part the City now plans to rebuild first. The full renovation plan lost its main funding partner in early 2025, and the piece that survived is the entrance at South 18th Street and Quarry Field, the one people walking up from the Flats actually use.
Getting in from the Flats
There are two practical ways in from below, and both end at Saber Way.
- The 18th Street entrance. The South Side Slopes Neighborhood Association's StepTrek directions say to cross South 18th Street at the crosswalk, turn right, and walk about 40 feet to the "South Side Park" entrance at Saber Way.
- The Serpentine Steps. From the top of South 21st Street, the 72 Serpentine Steps climb in sets of three up to Saber Way and the field parking lot. The SSSNA's 2026 Black Route walks them in the opposite direction.
If you want a longer climb before you reach the trees, the South 18th Street Steps go 138 steps up to Pius Street, and the lower 20 were rebuilt for an earlier StepTrek. The SSSNA ran StepTrek 2026 on October 3, starting from 21st and Josephine.
A loop through what the valley used to make
Friends of South Side Park publishes a self-guided hike it calls "a 30ish minute hike that includes some semi-steep ascents and descents, but generally easy." The official version starts at the top, at Arlington Baseball Field behind the Arlington Fire Station. From the Flats, the easier place to join it is the Quarry Field parking lot, about halfway around. Walked from there, the loop is a tour of the industries that worked this valley before it became a park.
- Quarry Trail. Climb the wooden steps from the lot and wind up past a wall the federal Works Progress Administration built in the 1930s. The 1998 tornado knocked down many trees along this stretch, but the blackberry bushes survived.
- The crab apple. Where Quarry Trail meets South Side Trail, the wide tree beside the trail entrance is the only crab apple left from the park's original 1960s planting.
- South Side Trail and Keeling Coal Trail. A narrow-gauge railroad once brought coal from the South Hills through an underground tunnel into what is now the park, then down an incline to 21st Street and out to the river. Along South Side Trail you'll see an old cistern and the railroad's piers. Keeling Coal Trail branches off as one of the park's most secluded routes, with small stream crossings.
- The vanished houses. About a dozen homes once stood along what is now South Side Trail. With no paved road, garbage trucks couldn't reach them in winter, and volunteers still dig up 60-year-old trash bags, glass and metal from the hillside. The Salisbury Connector Trail branches uphill to the Arlington Rec Center.
- Bandi Schaum Trail. The Student Conservation Association helps maintain this trail. At the bottom sits the Bandi Schaum Community Garden, built on an old Little League field and named for a beloved coach.
- Tombstone Trail. The surface is rocky because the Sankey Brick Company scraped off the clay soil to make bricks. The "tombstones" the trail is named for are tall paired pillars, all that's left of an aerial tramway that carried brick materials. The Friends' guide lists barrel making, coal mining, coke ovens, slaughterhouses, a glass factory and a bronze foundry among the park's past industries.
- Back down to Quarry. From the plateau you can look down on South 21st Street. Then the trail drops over natural rock steps and across a couple of streams that run year-round, and comes out at the Quarry Field lot where you started.
The same guide has a side stop called Jurassic Overlook, a valley so overrun with knotweed and grapevine "it looked as if dinosaurs could be roaming down there." Long before that, the St. Clair Incline carried pedestrians and freight up this valley from Josephine Street to Salisbury Street, until it burned down in 1935. The City's master plan puts the incline's lower station on Josephine Street near South 22nd Street. In other words, the Flats once had a direct ride up into this valley.
Why the 18th Street side goes first
The Quarry Field lot where the loop begins and ends is the site of the coming rebuild. The Friends' guide describes it as the future home of a natural-style children's playground and an improved entrance from South 18th Street. In May 2023, the City announced that the playground there had to be removed because of unsafe conditions and that the swings would stay.
The original Phase I was a joint project between the City's Department of Public Works and the Pittsburgh Water and Sewer Authority. In early 2025, PWSA pulled all of its funding. To keep part of the project going, DPW split Phase I in two.
| Phase IA | Phase IB | |
|---|---|---|
| Where | 18th Street entrance and Saber Way | South 21st Street entrance |
| What | Renovated entrance and parking, discovery garden/playground, relocated basketball court, new parking along Saber Way | Renovated parking, ADA-accessible boardwalk over green infrastructure, shared-use bike path |
| Status | Bid released and awarded in 2026 | No schedule posted |
The 21st Street half was always the more ambitious one. The Friends' trail guide still describes the original idea of removing about an acre of pavement at South 21st Street and catching stormwater in underground tanks and green infrastructure. Today that water runs downhill into the South Side Flats combined sewer system. PWSA's own South Side Park stormwater project page lists the project as "On Hold," with start and completion dates both marked TBD.
So the part that kept moving is the part the City could fund through DPW on its own, and it happens to be the entrance closest to the Flats.
Where the schedule stands
The City has been posting updates on its South Side Park project page for years. The most recent ones trace how Phase IA got back on track.
- May 24, 2023. The City says the Quarry Field playground must be removed because it is unsafe and that the swings will remain.
- March 3, 2025. After the funding change, the project goes on indefinite hold while DPW rethinks the scope with City Council and community groups.
- February 18, 2026. DPW moves ahead with Phase IA, posts it for bid, and expects construction to begin in early summer 2026.
- July 31, 2026. Construction "has been delayed slightly and will begin in September 2026."
The City's procurement portal shows "South Side Park Phase 1A Construction," project ID 2026-IFB-001, released Friday, February 20, 2026. The listing is marked closed and awarded, and its last addendum was posted April 6, 2026. September has come and gone since that July 31 forecast, and the project page hasn't posted a newer update, so check it before planning a walk that starts at the Quarry Field lot. That's where Phase IA work is planned.
The people already working the hillside
Most of the work in the valley so far has come from Friends of South Side Park rather than a construction contract. Goats have cleared invasive plants for weeks at a time between South Side Trail and Keeling Coal Trail. At Jurassic Overlook they are in their fifth year. After the goats leave, volunteers pull out the woody remains and roots so young trees can take hold. The group says it has planted 213 trees, 57 shrubs and 130 perennials, following an ecological restoration plan the Pittsburgh Parks Conservancy prepared for the valley.
This summer's Goat Fest drew the park's herd to Arlington Ball Field on Saturday, July 25, 2026, with music, an artisan market, food trucks and children's activities. Year-round, the Friends hold a volunteer workday every third Saturday and say they welcome "people of all ages, abilities and skill sets." You can join their update list at [email protected].
For more nearby walks, see our South Side Flats riverfront and trails guide, or head west along the hillside to the Mount Washington woodland walk most residents think they can't take.
If you live a short walk from the 18th Street entrance and wonder how a new playground and parking at the bottom of the park might figure into your home's value, Michele Leone follows these blocks closely and is happy to talk it through. Start with your instant home valuation, then give Michele a call about the details only a local agent tracks.
