40 mile trail that encircles Mt Hood. You will gain over 10000 feet, going up one glaciated canyon and down the next. It is a spectacular way to spend a few days. The views and experiences will be with you for a lifetime. And when the trail is not taking you past breathtaking views of the mountain, you will be wandering past fields of wildflowers, knarled wind-swept trees or the occasional waterfall. Remember that crossing glacial streams is easier in the early morning than late in the afternoon, due to the increase in snowmelt.
We took a snowcat ride from the base at Timberline Lodge to about 8500 feet. Some may call this cheating (and I'm among them), but it shaved a good hour or so and nearly 2,000 feet of staggering through slushy snow in the dark from what was still a long morning.
Ten of us crammed into the back of the snowcat, gear and all, and chugged our way up the mountain. We passed numerous early morning climbers who waved as we rumbled past (at least, I think that's what the raised hands were for. It was too dark to see if all fingers were raised in greeting by the tired climbers who were struggling up the mountain).
To best enjoy Mt. Hood and surrounding area, it is best to have your own transportation vs. a tour, so that you can explore on your own. Be attentive to rental car contracts, which may prohibit certain areas of Mt. Hood from being explored in their vehicle. However, most access roads to and around Mt. Hood are of good condition and are not prohibited by rental car companies.