Portland, ME hands down. Lobster, betches.
I grew up in Portland, Oregon, so of course. But I left and was grateful to get out. I think growing up there spoiled it for me.
Roddy
I’m from the Northeast but I still think Oregon. Its a bigger, more important city. Now that I’m living with someone whose family is from there, that just clinches it.
Maine. 90% of the time I hear someone say “Portland” they mean Maine.
Portland, OR and I live there.
Some Simpson characters were named after Portland streets; many streets were named after Civil War generals (Couch [pronounced “Kootch” for you Maniacs], Harney, Hooker, Grant, etc.).
Oregon.
I’m in the PNW so the inferior 
Maine version doesn’t come up much.
In my household it will be referring to Portland Maine only because my currently in college kid is at Bates, in Lewiston Maine, 45 minutes out of Portland, so I voted for that one. That said if I heard it out of my household I would assume it was in reference to the Oregon one.
I have no idea why but I distinctly remember thinking “Maine” when I heard “Portland” when I was a kid, and at some point it changed to “Oregon.” Perhaps when “Seattle” became a thing (to kids in the Midwest).
I think of Oregon, and I’m in New Mexico. I was thinking it was an east/west thing - my dad once lived in Maine, and around that time, I’d have thought of Maine - but now that so many have mentioned it, it did shift in the past few decades, as Seattle and Portland, OR became more prominent.
Oregon. Even though I’ve never been there, and have visited the one in Maine a handful of times. I’m a recent transplant to New England.
My pole has never spoken to me, ever.
I’m in Chicago, and it’s Oregon for me.
Or Isle of Portland.
I’m from Oregon so you know my answer.
When I hear “Portland”, the first thing I think is “Which one”? Sometimes it’s easy to tell which Portland from the context of the story, but both locales have their share of weirdness.
Concrete.
OR even though I’ve never been there but I have been to Portland, ME.
I’m from Alabama.
[QUOTE=Charlene]
I’ve been to Oregon but I’ve never been to ME.
[/QUOTE]
Maine, because I’m a native Maineiac!