Melting into the thick cushion of my light-blue butterfly chair, I pick up a copy of The New Yorker from my mahogany TV tray. The dense, dry articles are a welcome companion on this lazy afternoon. About midway through "The Talk of the Town," something becomes painfully clear: I'm hungry. Famished, even. I phone Lonesome's Pizza.

"And where do you want this delivered?" the pizza dude asks.

"Pioneer Courthouse Square," I reply. "I'm sitting in a big blue chair in the center of it."

The square across from historic Pioneer Courthouse has long been known as "Portland's living room." This weekend, it celebrates 30 years of service to pigeons, professionals, musicians and the odd transient (or seven) who flock there. On a recent Monday afternoon, I decided to see how Portland's living room measures up to my own.

A man in khaki pants and a Hawaiian shirt patrols the area with a rainbow "FREE HUGS" sign while a group of bros toss a red Frisbee. I return to The New Yorker column, hoping to enjoy droll ex-reporters writing lowbrow satire about New York politicians, but elderly doomsday hecklers on the northeast corner of the square prove too much of a distraction. I opt to accept the proffered free hug.

My pizza arrives—salami, banana peppers, shallots—drawing passersby like moths to a flame. Ever a polite host, I'm happy to share. A gentleman in a well-cut, pinstriped navy suit asks if free-hugs guy and I have colluded to offer free hugs and pizza. A man with a daffodil wrapped around his yellow-rimmed shades stops to explain why Portland is better than Seattle. A woman in a long hemp skirt sits on the off-white rug I laid out, and we watch a guided Segway tour roll through. I can hear a cop politely asking the 20-something man who'd been sleeping peacefully 10 feet behind me to move. (Living in Portland's living room is apparently illegal.)

I reopen my magazine only to be interrupted by a hobo wearing a khaki jacket and corduroy pants. He hits my wristwatch with a small placard, yelling something about hugs in gibberish. It's time for me to move to another room.

GO: Pioneer Courthouse Square celebrates its 30th birthday with "Singin' in the Square," a community sing-along led by Thomas Lauderdale and featuring Storm Large, China Forbes and Pink Martini. Sunday, April 6. 3-5 pm. Free.