4 Downtown Pittsburgh alleys worth cutting through

Alleys get a bad reputation. The narrow side streets are often associated with illegal behavior, trash, and darkness. Not exactly the kind of place that encourages a leisurely stroll.

Downtown Pittsburgh has its share of the type of alleys you'd expect in a city, but it also has some that may be even nicer than some streets with sidewalks and shops. Downtown Pittsburgh is a walker’s paradise, especially when compared to other midsize Rust Belt Downtowns. It only takes about 15 minutes to walk end to end, and there are several shortcuts through alleys that should be taken advantage of.

Some Downtown alleys offer unique and pleasant experiences that are hard to replicate. And some even have businesses to patronize, public art to behold, and unique architecture to enjoy. Here are City Paper’s choices of Downtown alleys that are worth cutting through.

Cherry Way (in between First Ave and Boulevard of the Allies)
This small section of Cherry Way near the Monongahela River feels like a step back in time. The road is made up of gray bricks and the surface is impressively uneven, even as the red-brick sidewalk next to it is smooth and charming. The historic Heartly-Rose building, which was built in 1907, sits in the middle of the alley, and harks back to a time when Downtown wasn’t dissected by expressways. It's a surprisingly quiet and pleasant place to stroll.

Garrison Place (in between Liberty and Penn)
This alley is best experienced by looking up. Garrison Place serves as a useful shortcut to get from Liberty Avenue to the Penn Avenue Cultural District, but don’t just look straight ahead. Above the alley is a dazzling light display best seen at night. The public art project was converted from the light display that used to be on the Rachel Carson Bridge. Florescent blues, purples, and whites light up this alley.

Strawberry Way (in between Smithfield and Grant)
Probably the most popular alley in all of Pittsburgh, this three block stretch has been a pedestrian paradise ever since they made most of it car-free a few years ago. Now it is part public-art project and part lunchtime plaza. It’s also home to not one, but three businesses to patronize (a rarity for any alley). The somewhat hidden Villa Reale bar can be accessed from Strawberry Way, as can the Tom James Company clothing store, and The Commoner entrance is on the alley. In 2017, the national transit and urban planning news site Streetsblog USA awarded Strawberry Way its Best Street Transformation, People’s Choice award.
Tito Way (in between Liberty and Penn)
There is a bit of construction going on nearby on Penn Avenue, but Tito Way still shouldn’t be missed. It’s a needed shortcut in between Liberty and Penn Avenue because the block between Seventh and Ninth streets is fairly long, so it gets a lot of foot traffic. Also, along the wall that makes up the back of the Benedum Center, there are public art projects, including the mesmerizing Cell Phone Disco. Dots of colorful lights fill up your vision. And as you exit Tito Way and onto Penn Avenue, you can cross the street and enjoy some free sparking water from the Water Cube.