Skip to Content
Streetsblog California home
Streetsblog California home
Log In
Parking

Parking Madness 2019 Round 1: Portland vs. Pittsburgh

We're continuing with our hunt for Most Improved Parking Crater today, slowly but surely narrowing down a list of 16 candidates to find the urban parking lot that has become a beloved cityscape rather than a cement crater filled with cars.

Today's matchup is a little different because it features two central civic spaces that were once nothing but asphalt.

Before we get to it though, voting is still open for yesterday's competition pitting Houston vs. Boston (Minnesota and Oakland have already moved onto the second round).

parking madness 2019
false

Now on to today's competition:

Portland

P-town's Pioneer Courtyard Square was formerly a low-rise parking deck.

Reader Jay Shuffield, who submitted the below photos, said, "There's probably nothing that challenges Portland's Pioneer Courthouse Square emerging from the site of a full-block parking deck to become the city's central civic space."

portland before
false
portland after
false

Pioneer Courtyard Square calls itself "Portland's living room" and the city's "most visited park." The square hosts 300 programmed events per year, according to the nonprofit group that oversees the space.

Pittsburgh

A similar conversion has taken place in Steel City's famous Schenley Plaza.

pittsburgh after
Photo: John Altdorfer, Schenley Plaza story time
false

Reader Laura Ellis nominated this space, saying:

The five-acre plaza is located on what was a large, 280-space parking lot in Oakland and situated between the University of Pittsburgh, Carnegie Mellon University, Phipps Conservatory, and the Carnegie Museums and Library. The Pittsburgh Parks Conservancy, in partnership with the City of Pittsburgh, transformed the space, and today this much-loved community greenspace attracts hundreds of thousands of visitors every year, providing gathering places, entertainment, and a grand entrance to Schenley Park.

In addition to a one-acre green space, the park contains dining kiosks, a carousel, public restrooms and a full-service restaurant. In other words, it's a big improvement over a parking lot.

But can it top Pioneer Courthouse Square? Let us know which deserves to go on to the second round. Vote now!

Stay in touch

Sign up for our free newsletter

More from Streetsblog California

What Is an E-Bike, and What’s an Unlicensed Motorcycle: A Parents’ Guide

The holiday shopping guide for anyone in the e-bike market.

December 10, 2025

Wednesday’s Headlines

YIMBYs, and Widenings, and Bike Cops, oh my!

December 10, 2025

Caught on Video: AC Transit Operator Appears to Assault Cyclist

Bus driver uses bike lane on Foothill to queue jump slow-moving traffic, tailgates and honks at a cyclist in the bike lane, then nearly runs him over.

December 9, 2025

Report: Speed Camera Programs Working in San Francisco, Floundering in Bureaucracy in L.A.

Great progress and success in the Bay Area, while So Cal lags

December 9, 2025

Tuesday’s Headlines

Only one headline about how LA is actively undermining safety today.

December 9, 2025
See all posts