Steven's Peak-bagging Journey

August 2, 2026

158m

Orcas Island, WA

Pioneer Hill is a residential area on the eastern half of Orcas Island but the highest point boasts over 100 m prominence to qualify as an independent summit. I don’t think the peak itself is officially named, but the road that provides access to the houses is called Pioneer Hill Road. This was the 2nd objective when I planned to slam across all P100m hills on Orcas Island in one day. Earlier in the day I had already done Entrance Mtn. and now I was driving up the access road. As expected this was also a private road but thankfully it was not gated. Clair decided to stay in the vehicle with Cheesecake since this would be trespassing and there’s no trail whatsoever leading up to the high point.

I didn’t drive all the way up since it would bring me closer to the higher houses. I simply parked on the shoulder of the road directly due east of the high point and then dashed up the forest. The bushwhacking was very manageable and I was completely in the forest until basically the very summit where I could see one house to the immediate south. This was a “trash bag” that hits all the categories – no view, unofficial name, bushwhacking and trespassing.

Upon returning I quickly drove away, but before doing Rosario Hill I had promised Clair to drive her up Mt. Constitution, the highest peak on the island. I had already done that drive-up back in 2016 so I’m not going to provide a separate trip report. There’s nothing really worth noting anyway but we did get to walk the cat for a bit.