I’ve been living about 35 miles from Mt. Hood for the last 35 years, and have been to Trillium Lake quite a few times. But I live on the Washington side of the Columbia, which is even nicer in many ways .
It was October, very rainy, and the only skiers there were myself and the USST. Palmer Glacier was the only thing open. One of the US coaches told me that Mt Bachelor was opening that weekend and it would be all snow there, so off I went. There was no lift on the top half back then, but the snow was great and well worth some hiking.