Cloud Cap Inn is a 15 mile point-to-point trail located near Mt Hood, OR that features a waterfall and is rated as difficult. The trail is primarily used for snowshoeing and is accessible from November until April.
Note: this is basically the eastern part of the circumnavigation of Hood.
Feel like something challenging that'll leave you sore and amazed? Start out at Timberline Lodge, and head right at the PCT sign. 15 challenging miles later, you'll have crossed streams, battled heavy winds, had amazing views of Elliot Glacier, hiked Gnarl Ridge, and arrived at Cloud Cap Inn. Park a car and do it as a point-to-point. Or if you're training, hell, try all 30 miles of pain!
It's beautiful, though I'm not sure I'd make the trek in the winter months if not *completely* prepared: I've done it as a hike in the warmer months, but you might want to have a little mountaineering knowledge if you're trying it in the winter.