Pittsburgh, PA

We’re lucky to have a number of beautiful parks here in Pittsburgh! Schenley Park is one of my favorites because it has miles of wooded trails and stunning century-old stone bridges. It’s the perfect spot for hiking, running, relaxing, and a bunch of other outdoor activities. Plus, after soaking up nature, you can head right across the Greenfield Bridge to grab a pint and a bite to eat at Monday’s Brewing (yup, it’s open every Monday!)

THE HIKE: Schenley Park Loop

Length: 4.3 miles
Elevation Gain: 400 ft
Difficulty: Moderate
Time: 1.5-2 hours
Trail use: Hiking, biking, running

Where to Park: There’s plenty of street parking around Schenley Park. If you want to follow these trail directions, park along the road on Overlook Drive, which is free. Other places to park where you can pick up the trail are free parking at the Anderson Playground (the Dino Playground), or paid street parking by the Schenley Visitors Center. All of these locations have either a porta-potty or a full bathroom (Schenley Park Visitors Center).

The Route: There are miles of interweaving trails through Schenley, so you can easily do a short loop or extend for a much longer outing. This is one of my go-to loops that incorporates both the narrow wooded trails and the wider bridle trails and passes some of Schenley Park’s iconic features.

Start off on the Bridle Trail just off of Greenfield Road. Follow this wide trail as it curves around the cliffside overlooking the Parkway. This is a popular trail and you’ll likely be sharing the way with runners, cyclists, and other groups. After following downhill for about 0.8 miles, you’ll encounter the first historic bridge of your hike. This bridge, along with several others in the park, was built in the 1930s by the Works Progress Administration during the Great Depression. At one mile into your trek, you’ll reach a trail junction. To the right is the swimming pool. Stay to the left, getting onto the Upper Panther Hollow Trail and passing under a bridge. After popping up on the other side of the bridge underpass, the Anderson playground will be to your right, along with a water fountain and a porta-potty.

Continue along the Upper Panther Hollow Trail, another very wide path, as it passes under another bridge and follows along the curve of a hillside. At 1.8 miles, take a narrow path to the left as it leads down into the hollow. To the right is one of the stunning 1908 historic bridges that are iconic to the park. Continue straight, up the hillside and over another wide path. To the left is a large rock, whimsically painted like a sitting bird. Continue straight ahead onto a cobblestone slope, now getting on the Steve Falconi Trail. Continue along this single-track trail. This natural path is less busy than previous trails but is also more rustic. At 2.7 miles, the trail lets out beside a pavilion and West Circuit Road. Straight ahead is the historic Westinghouse Memorial Fountain. Continue along the road briefly, rounding the bend to the left to walk along the sidewalk along Schenley Drive. After 0.1 mile, the quaint building to your left is the Schenley Park Visitor’s Center. This is a great spot to grab a bite to eat, learn more about the park, or just use the restroom.

To continue your route, follow the cobblestone path behind the building back down into the park. Take the stone stairs that descend into the woods. In the early spring, these stairs are surrounded by bluebells. Cross over the Lower Panther Hollow Trail and keep heading down the stairs. To your right is the other of the stunning 1908 bridges. At the bottom of the stairs, turn right onto the unnamed trail and follow through some wetlands and a small pond. In several hundred feet, the trail opens up onto the Panther Hollow Lake, a popular spot for fishing and relaxing. Follow the trail as it circumnavigates the lake. Now on the Hollow Run Trail, bear slightly right to continue away from the lake and along a small stream. At 3.6 miles, the trail curves up and reaches a junction. Turn right to get on the narrow path that leads along the stream. On maps, this is also called the Hollow Run Trail, but in person, it has a sign for the Ponticulus Trail. This is an incredibly beautiful trail that meanders along the stream deep in the hollow and is less busy than the rest of the park. It’s a great place for seeing wildflowers and amphibians. Finally, the trail ends in stairs that lead up to Barlett Street. Turn right and follow along Bartlett Street for 0.2 miles to complete your loop.

This is just one of the many route options in the park!

Other Attractions: Schenley Park has a lot to offer! Some other spots that may interest you outside of hiking are the very cool and newly renovated Anderson Playground, the ever-popular disc golf course, numerous picnic pavilions, sporting fields, a swimming pool, and more! Just outside of the park are the stunning Phipps Conservatory, which has a free outdoor garden to walk through, and the Bob O’Connor Golf Course, an affordable 9-hole course open to all.

THE BEER: Mondays Brewing Taproom (Greenfield)

Address: 563 Greenfield Ave, Pittsburgh, PA 15207
Distance from Trail Head: 0.6 miles, 2 mins 
Website: https://mondays.beer/
Food?: Full Menu, operated by Smashed & Fried
Details: Street parking, wine and cocktails, NA options, indoor seating only, no pets

A guarantee at Mondays Brewing? You can always get a good beer on Monday! Monday’s Brewing originally opened in Peters Township in October 2020. They managed to find their footing during a difficult time in the service industry and have grown enough to open a second location. They found the perfect spot in Greenfield in the former Hough’s Taproom, a long-standing staple of the neighborhood. The huge taproom allows Mondays to grow in ways that their cozy Peters Township bar can’t. They have a full kitchen operated by Smashed & Fried, offering a menu of burgers, BBQ, and seafood.

Anchoring the space is a huge U-shaped bar where the Mondays team serves up 20 taps of their own brews along with some sampling of other local breweries. They are also fully stocked with locally made ciders, wine, seltzers, mead, and spirits. There are even some locally made soda and ginger beer options for the non-boozy.

Mondays is a great addition to the Greenfield neighborhood and we can’t wait to see where they go from here!

Looking for more Hikes & Hops in Pittsburgh? Check out Settler’s Cabin & Altered Genius Trailside, Dead Man’s Hollow & Firewhistle Brewing, North Park & Cinderlands Taproom, and Best Hikes & Hops in Pittsburgh!

Looking for more adventures in Pennsylvania and beyond? Check out my new book: Beer Hiking Pennsylvania and New Jersey