With easy parking right off Hwy 35 on the east side of Mt Hood, Bennett Pass is a perfect destination for a straightforward lap on cross country skis, snowshoes or accessing easy backcountry terrain for skiers and boarders. 

Bennett Pass Road is a well-graded 5.1 mile out-and-back with several trails branching off of it farther out. Dogs are allowed on leash. This trail starts in the sno-park off of Highway 35, near Mt Hood Meadows. A sno-park permit is required in the winter months.

The historic road is the western boundary for the Badger Creek Wilderness and the northern boundary for the White River Unit of the Mount Hood National Recreation area. 

The first part of the trail is in the trees, but as you climb you'll get views of Badger Creek Wilderness and there's a viewpoint near the end off the trail of Mt Hood.

This is a great option early in the winter because it's at a higher elevation and tends to get good dumps before other areas.

Trail map: https://www.fs.usda.gov/recare...