I saw some guy that looked kind of creepy while I was riding my bike along the trail on the way home after work last night (Oct. 28th) about 5:45 pm. He matches the description except I don't remember what he was wearing and he may have been in his 20s. He was walking along the trail and fiddling with an ipod and ear buds. He looked like he might be high (or something), disheveled and homeless.

A guy flashed my late wife once. She gazed at the display, smirked, and said "It looks just like a penis, only smaller." The guy fled.

"Old Ben"

Sounds like your late wife was fantastic! Quick on her feet and composed in a surprising situation. I wish I could be that way.

I wonder where on the trail this happened - It would be nice to know just to be extra alert around that part of the trail

The homeless population in the upper reaches of the trail are using the creek for their home and the surrounding areas for their toilet.
I was horrified to find piles of used toilet paper and feces strewn about literally FEET from where kids at Landels School can play.
Another homeles latrine is in the foliage on the east side of the wooden cal trans bridge 9yes, that's what that smell is all the time)
A clean sweep of the homeless camps is needed along the creek and trail. I would love to show the authorities where the few I know of are.

I also recently saw a group of guys loitering and drinking around sunset near the Evelyn Avenue entrance to the trail. They probably got their alcohol at the convenience store just down the street.

They weren't bothering any cyclists or pedestrians at the time, but some trail users might feel uncomfortable with a group that size there in the evening.

Stevens Creek trail is long . Some areas is OK but some places looks bad , unclean , too dark at 4 pm (for a big trees o a lot of bushes). I think Homeless is a Social problem in US , nothing to do with trails .
For a Homeless , every public place looks a bedroom o restroom .My experince in differents Countries is , If you want a safe public areas , clean every week , remove bushes or forest ,Police need walk sometimes a week to check some areas . Mountain View is a beautiful city , but nothing is perfect in the Planet Earth ...because Human Beings living there...

You mean you actually want the police to get out of their cars and walk the trail? Their is probably something in their contract that prohibits that or kicks in $100 extra an hour. Otherwise, I'm all for a police state crackdown and clear cutting of the trail areas like you suggest.

Police in other towns use bicycles. Those would be faster than walking, and still trail-friendly.