I made my first trip out to the Jackling House on a sunny day in Winter. After making the long drive up 280 North I finally arrived in Woodside. The area reminded me of a little yuppie town trying very hard to show off a rustic appeal. There were lots of shiny, motivated people in neon spandex biking around town. Most of the cars I saw were a lot nicer than my own and most of the people I saw seemed domestically friendly. The presence of these familiar sites caused me to feel weirdly at ease as I drove down the road toward my destination.

Once I made it to the mansion I parked my car nearby and strode up to the front gate, pondering whether anyone really watches that security camera. Briefly I glanced around to make sure that the neighbors were not looking and snuck into the property. After standing and examining the exterior of house for all it is worth, I started to look for an entrance. Turns out I was in luck because someone else had already removed a board, opening up access to the back door. Entry was easy.

Once inside my first sight was the keyboard of the massive Kilgen and Son pipe organ. Somehow I should have been scared as I had no idea what I would encounter in that house. But it was such a beautiful day outside, it seemed as though there could not be anything harmful hidden inside this endearingly decrepit little mansion.

As I slowly and cautiously progressed through the organ room I entered Steve Job’s old dining room. This is one of the best parts of the house since there are so many relics reflecting the early days of Apple. Old floppy disks laying around and an old check book. There were quite a few magazines with Jobs’ face on it. Perhaps if I were a celebrity I would collect these too? If I did, would I want to leave them behind? It was an odd experience examining a local celebrity’s old junk, it felt almost like digging through the house-wares section at Goodwill.

Looking around the kitchen I saw a more of Steve Jobs’ old possessions. Lots of cobwebs, peeling linoleum. I tried to take a photo of the light fixture just for the sake of taking photos and then I wandered to the next portion of the house that led to a hallway. The hallway revealed a very antique-looking elevator, which I found to be quite lovely though I could not manage to get a good photo of it. It struck me as odd that one would want an elevator installed in a two-story house. Perhaps this is an early 20th century sign of luxury…or…something? :P

As a walked up the steps to the second floor I noticed a lot of bathrooms. Actually, that is one thing that sticks out for me about the mansion. Lot of very nicely decorated, ornate guest bathrooms. There was also a bunch of bedrooms, a sophisticated “Abestos” graffiti warning on the wall and some other rubble that has since escaped my memory.

I finally circled back down the stairs and entered the old living room, complete with a clunky 1980s TV set and VHS tapes to match. There were lots of vinyl stacked in the corner though I did not recognize any of the recordings. There was also a massive pool table. Really no comparison to a 21st century mansion that is likely to include an in-door videogame arcade, LAN room, Olympic size swimming pool, and other goodies. But still, endearing in an old-fashioned lost-and-forgotten sort of way.

It seems that the only thing I feel I missed out on was exploring the tunnels underneath the house. But I was alone and remembered some rumors about wild animals living down there, which was enough to scare me away. I really hope that they restore this house, though in the end it will not look as cool as it does now.