This will be an exploratory hike, at least in the half. We will hike up Alamo Canyon (t104)...then head up Caballero Canyon (t103)... though official routes, neither have a trail. We will angle off up into Caballero Canyon North and follow that drainage up to West Side Road, enjoying a really delightful meadow/hardwoods section. At West Side Road we will scale the huge rock strata waterfall, cross the road and amble up through the old mining site... spending a little time among the adobe/rock house ruins.
From the old mine site, the exploration begins. The idea is to follow the upper drainage as far as we can, then access a ridge for the final push up to the Observatory. This section could be an overgrown mess.
Once at the top, we have the option of retracing our path or heading down Alamo Peak Trail (t109) to access Alamo Canyon Trail (t104) for the hike back to the cars.
This will be a very long, very difficult, very tiring hike... over 20 miles with over 5,000' of climbing, all off trail. The pace will be moderate. If you come, bring along lights in case you need to finish the walk in the dark!
I might set up a shuttle up on West Side Road to allow for a shorter finish, if desired.
This is not a hike for beginners. If you are not in shape, this hike will hurt you... it will likely hurt me!