Sleepy Hollow Trail

Great views of Terra Linda and the bay from this trail. This is the perfect place to go for a run or walk with your dog! Not to mention everyone on the trail is extremely friendly

Sleepy Hollow is a fun, if short, trail. Lots of giant hills and people walking their dogs. The view can be great, stretching out all the way to the highway and the bay.
Not a huge fan of the lack of rest stops/​water fountains, but if it means less people, I’m all for it. I don’t want this place to turn into Mission Peak.

Great views in all directions. On one side is the civic center, lagoon, and Northgate Mall. Into the other is Mt Tam. The trail is nice and wide. Its a dirt road though pretty smooth. Easy biking once you make it to the top of the ridge. Can be very windy so be prepared

What’s listed here as the «Sleepy Hollow Trail» is actually the «Sleepy Hollow/​Terra Linda Divide» (or vice versa). The trail can be accessed from numerous points in San Rafael (e.g. Ridgewood Drive near Sun Valley School), but I’m most familiar with access points in Sleepy Hollow.
Sleepy Hollow is the unincorporated part of San Anselmo known for big, horse-​friendly property, no street lights, and hot summers. All of Sleepy Hollow is either on Butterfield Road or can be accessed via Butterfield Road, and this series of trails is no exception.
The simplest Sleepy Hollow trail access is about ½ way up Fawn Drive, where a trail access beckons on your left. Park, access the trail there, then walk to your left and you can get a great hike on the ridge-​top, almost all the way to the top of the mountain. There, you’ll encounter the monstrosity of a fence that James Hetfield (Metallica) erected to keep people from hiking on the trail that runs through his mountaintop, undeveloped property. Don’t get me started on that…
There’s a big effort to erect a bike-​friendly trail around the Hetfield fence, but until that’s done, it’s best just to turn around at the top and head back the way you came. Dogs are welcome on this trail (and its offshoots), as are bikes and hikers. If you see me, say hi.