Alright, you've heard it all before... "Help me choose <fill in the blank>." I am ashamed to say it, but I am defeated without you guys. Hint: I am married...

Anyway. I have a timeshare week to book in the next few days before we transfer our ownership to our son (who doesn't want this week). I have looked and looked.

There has just dropped into availability 2 weeks that really appeal to me - both in Welches,OR (Mt. Hood/Columbia Gorge) - one in early August, one in early October. But which one?

DH wants to take one of those family-research pilgrimages to Hungary in September, so either week is close to his dream. But we both love mountains, wineries, day hikes. And - crowds diminish, maybe shoulder season; but you have: mild early fall weather - mellow warmth, drier, cool night, some fall color. In this area, is August too early? October too late?

Otherwise, I will need to choose either Tahoe in late May (been there a lot), San Diego in late May (ok, that could be good, but I grew up in California), or maybe just a vacation without that grouchy old man (BOOOORING! He is my best friend.).

Any comments on these two times and location?

Question: In this area

What the heck. Disregard that last line.

I'd take a chance on August for Welches. Weather is iffy no matter when but you have a better chance of nicer and warmer days. October could be rainy and will definitely be cooler at that elevation.
Are there wineries up by Welches? I've never heard of any but they do pop up all over the place, don't they? Or are you talking about popping over to Hood River?

<sigh> Let's just say we are still negotiatiating, DH and me.

At this point, Welches (Mt. Hood) would have to be Memorial Day week. The other times are gone. Is that still pretty rainy?

I've never had such a problem setting vacation plans. This time we just seem to have very different ideas, I guess. And none of those ideas mesh with availability, lol.

Thanks for the advice.

For many years we had a vacation home just several miles from Welches.

We spent many Memorial Day weekends there, and had beautiful weather.

I can't guarantee it though - this has been an unusually rainy summer this year. This weekend however, is spectacular