Why would she rip your balls off for something as romantic as a picnic or a symbolic place?

Hey Boneprone ~ There's a private, custom built yacht called the Crystal Dolphin that docks in Portland and is part of www.portlandspirit.com
You can dine 50 on a two and a half hour cruise with beer, soda & wine beverages included (coctails extra), and simple 3 course meal with choices.
All for $3850.
Then if you want you can hire a cheesy cover band for an hour or something.

I don't know your budget, but feeding and entertaining her friends sounds like a big undertaking, and this would be a really memorable way to accomplish everything.

Maybe take her to the place were you two went for the 1st birthday you were together.

MT HOOD , if she likes sking thats not a bad idea.