Rachel Dresbeck wrote favorably of the magazine in her 2007 book Insiders' Guide to Portland, Oregon.

[1] Planning and research for the magazine included conducting 200 interviews with residents of Portland, in addition to raising US$40,000 from angel investors.

[5] Scott Vogel served as the magazine's first editor-in-chief,[7][11] and left Portland Monthly in late 2004 to join The Washington Post.

[3] The magazine has reported on the effects of methamphetamine abuse in Oregon, and Enron's usage of the electric utility in Portland.

[21] Writing for The Columbian, Angela Allen commented that the first issue of the magazine "shows attitude and literary writing, tosses off lots of names, does a terrific fall culture calendar and digs into a couple of issues, including the Trail Blazers", but was also critical, noting: "Its design is crowded and the type is too small to read for most of us without wearing a pair of 'reader' specs.

"[4] Tom Boyer of The Seattle Times described the magazine as "a smart mix of reader-friendly features and award-winning journalism".

[1] Writing in The Oregonian, Steve Duin commented that he appreciated the lists published in the magazine: "Because I'm addicted to lists – and the bigger the better – the best part of my month is the morning that copy of Portland Monthly lands like a wounded halibut on my desk.

[23] In her 2007 book Insiders' Guide to Portland, Oregon, author Rachel Dresbeck wrote that the magazine "maintains an excellent calendar" of events going on in the city.

[24] In July 2007, Nicole Vogel was a finalist among nominees for an individual entrepreneurship award from the Oregon Entrepreneurs Network.