When I went into retirement from TBD I changed my name, so he probably won't find me.
I'll give you five suggestions: Wine, Dine, Gorge, Coast and Hood.
Mt. Hood and the coast are within 1 1/2-2 hours drive from Portland. They both make good day trips. Just leave before 10am to avoid the traffic. Also, the coast and Mt. Hood tend to be 10-20 degrees cooler than inland. So dress in layers. My suggestion for a beach town to go to...Seaside or Cannon Beach. There's also Astoria up north a little. The Goonies house is there.
The Columbia Gorge is about 1/2 hour or more from Portland, depending on where you end up. Hood River is kind of a neat city with good food and wind surfing. I like to sit and watch the wind surfers. Hiking to the top of Multnomah Falls is kind of a challege but well worth it. There's also The Vista House with great views of the Gorge.
Out west about 30 minutes or so is wine country. Great views and great wine! Here is a map of the wineries.
Portland is known for it's great food and breweries, wineries. The Bite of Oregon is going on this weekend. The local wineries, restaurants, breweries will all be there. There are also a ton of food carts around that have decent food as well. "Big Ass Sandwiches" sells out every day and always has a line a mile long.
Depending on which Hotel you are staying at in Portland, if it's close to Pioneer Courthouse Square, you can check out local bands playing during the lunch hour.
Don't let the clouds discourage you. They will burn off by the afternoon. But it sounds like it will be in the 80s this weekend and next week...perfect.