According to the information I found on the internet, the Dipsea Trail is one of the "must hike" trails in the bay area. For more information, see the Dipsea race web page. http://dipsea.org/
I'll say the following about Dipsea Trail.
1. I didn't enjoy hiking Dipsea - parts of the trail is too urbanized.
2. It is quite strenuous, with 2000 ft of climbing to be done each way.
3. The Trail isn't well marked. I got lost several times, including walking up someone's driveway, thinking that was the trail. I'm sure the situation with lost hikers was as annoying to him as it was to me. I can't believe that I'm the first lost hiker that's walked up to his driveway.
Dipsea is famous or infamous for the stairs that begin the Trail in Mill Valley. The stairs are in multiple segments. Here's one of the segments.
Dipsea Trail is over 100 years old, and at one time, the trail must've been considered to be in complete wilderness. However, the first mile or so of the trail is basically in the suburbs of Mill Valley. One of the reasons that it's easy to get lost is that after climbing up one segment of the stairs, the stairs terminates at a suburban street. The next segment of the stairs will be somewhere down the street. The problem is that for a first time hiker who doesn't already know the trail, there's often no sign that tells the hiker to go left or go right on the street to find the next segment of the stairs. The picture above shows that for this segment, the correct answer is "turn left", and the next segment of the stairs is 100 yards down the street, next to the postal truck.
First mile of the trail is sometimes paved, sometimes not. When it's paved, it's part of one street or another. Here the street/trail leads past someone's driveway. In one part of the trail/street, someone put set up a basketball pole, so the neighborhood kids can play basketball. 
The craziest part of the Dipsea Trail has to be the 1 meter tall drainage pipe that cuts across the trail. The pipe drains water from the roadway, and it is set up down a 30 degree slope. However, in the process of laying down the drainage pipe, the Dipsea Trail was torn up a bit, and it was difficult to find the correct/safe spot to climb over the drainage pipe to continue hiking. Here the Trail resembled less of a nature hike, but more of a steeplechase course. 
About 7 miles from Mill Valley, The Dipsea Trail ends at Stinson Beach. At this point, I turned right around and got back toward Mill Valley.
Perhaps if I lived in Mill Valley, in one of the houses whose driveway I walked by, then Dipsea Trail would be one of my favorite trails. It would be very convenient to be able to do a lot of hiking right from one's residence. However, having driven 60 miles to get to Mill Valley to hike this historic trail, I can't say that I enjoyed hiking the Dipsea Trail. The complete urbanization of the first segment of the trail, with the ultimate symbol being the insane drainage pipe, completely soured me on the Dipsea Trail.
So all I can say is - I've done it, don't think I'll do it again.
Thanks for sharing the experience! I agree it can be disappointing if one was expecting nature, but saw houses instead. From the map it looks like part of the trail is in or borders the Golden Gate Recreational Area, but not where the trail begins and ends. At least you get to see the ocean and the beach! Nice.
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