Heather, I agree with much of what Bob B. just posted, but how far south are you thinking of going? By late May, the first 40 miles should nearly snow free. However, the west shoulder of Mt Hood (MP 2098-2102) has a 4 mile stretch that has been the undoing of many experienced hikers. It's the part of the trail that is above 5200' elevation. Have a great hike, Jerry