Nothing extreme - the hilly sections for the most part are rolling hills.
I think the toughest part may be after you do the lap of Lake Sammamish and then you climb up Village Park drive and along Lakemont Blvd toward Coal Creek Parkway - it's not the steepest road in that area but coming toward the end of the ride that may feel difficult.
Some good training loops would be (from shortest to longest):
- Laps of Mercer Island (counterclockwise is hilliest)
- Laps of Lake Sammamish
- The Chilly Hilly course on Bainbridge Island
- A lap of Lake Washington.
If you're not comfortable doing a lap of Lake Washington (a bit over 50 miles) between now and the Livestrong Challenge I think you'll find the Livestrong Challenge to be a, well, challenge.