The hike around Three Fingered Jack is a popular 21.5 mile loop, starting at the Pacific Crest Trailhead at Santiam Pass. You can also start the hike at Jack Lake Trailhead, however the road up to Jack Lake is long and rough, so even if you’re coming from Bend or Sisters, it will still take less time to drive to Santiam Pass. At the Santiam Pass trailhead, don’t forget to fill out your wilderness permit if you are day hiking between June 15 and October 15. If you are backpacking, you will need to obtain a limited entry permit beforehand. ​The hike starts out on the Pacific Crest Trail, heading northbound through bushels of bear grass and silvery tree snags that remain from the very large B&B Complex fire in 2003. The Pacific Crest Trail will continue gaining elevation, as you head up the southern flank of Three Fingered Jack.