7. Hill District history

Distance: One to three miles

Go: Use this route from Urban Hike of the Middle and Lower Hill.

Level of difficulty: Moderate

Highlights: The August Wilson House, Freedom Corner and the former Crawford Grill are a few of the local landmarks on this hike. A restoration project is underway at The August Wilson House on Bedford Ave. to restore the boyhood home of the late playwright as a gathering place for artists. Stop by the nonprofit Ujamaa Collective on Centre Ave. or grab a bite at Grandma B’s Cafe (2537 Wylie Ave).

8. Wilkinsburg walkabout

Distance: One mile and up

Go: Start on South Ave. near Nancy’s East End Diner (616 South Ave.), then veer to Hay St., Ross Ave. and Wallace Ave. This route from Urban Hike offers street map and landmarks along the way.

Level of difficulty: Easy

Highlights: Schoolchildren raised $800 in 1916 to pay for the Penny Lincoln Statue you’ll find in Graham Field on this hike. The statue was rededicated in 2001 after students helped raise money to refurbish it. Another spot of note: The Wilkinsburg Train Station, built in 1916. The Wilkinsburg Community Development Corporation is raising money to refurbish this Beaux-Arts building on Hay St.

The welcome sign on Troy Hill. Photo by TH Carlisle.

9. Troy Hill trek

Distance: One to three miles

Go: Find parking along the North Shore portion of the Three Rivers Heritage Trail near the Herr’s Island railroad bridge, then use this Urban Hike route for inspiration.

Level of difficulty: Moderate. Expect to ascend steps and hills.

Highlights: Troy Hill’s rich history is on abundant display here, as you pass by St. Anthony’s Chapel, which holds the largest collection of Christian relics outside the Vatican. Check out “The Women of Troy Hill,” by Clare Ansberry, which is an ode to the work ethic and values of this historically German neighborhood. After all that walking, one option for a quick meal: The Pear & the Pickle (1800 Rialto St.), with made-to-order sandwiches, or try Scratch F&B at 1720 Lowrie St.

10. Highland Park

Distance: About three miles

Go: Highland Park offers fun year-round, and this loop is no exception, with a mix of dramatic architecture, wildlife and stands of trees.

Level of difficulty: Moderate

Highlights: Try the loop around Reservoir 1, which was built in 1879 to provide public drinking water. The area grew into a popular gathering spot, and about two decades later, the City of Pittsburgh created Highland Park. Grand architecture is showcased throughout the park. The welcome sculptures at the Highland Park entrance are the work of artist Giuseppe Moretti, who lived in Pittsburgh from 1916-24.

Craving coffee? Though not in the park, Tazza D’Oro Cafe & Espresso Bar (1125 North Highland Ave.) is just a half-mile away.

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About The Author

Editor and writer

Kimberly Palmiero is an independent journalist and business owner. She spent 25 years working for media companies in Pennsylvania and Illinois, most of that time as an editor on news desks. She left Trib Total Media in 2016 as a managing editor. A passionate journalist, she also is board president of the nonprofit Press Club of Western Pennsylvania (westernpapresclub.org). In 2009, she founded a small business which acquires, refurbishes and rents residential property. She enjoys running through city neighborhoods just after dawn. She may or may not cap off runs by drinking several espressos She lives on the North Side.

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