http://www.portlandhikersfieldguide.org/wiki/Tilly_Jane_Hike

Activity Notes

This is a strenuous mountain hike.  4500 feet elevation gain in 6 miles (12 miles round trip). As it's a fall hike, be prepared for changeable weather.   Bring extra layers, hydration, sunscreen, etc.   Poles recommended.

We're going to head for Tie-in rock up above Cooper Spur, but will turn around earlier depending on our pace.

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From Oregon Hikers:

Most hikers reach Cooper Spur, the highest point on the mountain reachable by trail, by starting from the Cloud Cap Inn for a moderate 6.5-mile hike. This hike takes a longer and more difficult approach, starting at the Cooper Spur Ski Area and gaining over 4500 feet in less than six miles. No two ways about it, this hike is a calf-burner, with almost as much elevation gain as Mount Defiance in a similar distance! Make sure to bring sunscreen, as there is no shade for the majority the hike.

Other Information
Driving Distance from Portland 73 miles
Driving Time from Portland 1 hours
Distance - Round Trip 5 miles
Expected Duration Car to car in one day
Awards Qualified Mt. Hood Award, Wild Ones