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Summary - Summiting Monte Carlo in the winter is easy as long as you are good with an eight mile round trip with a 3000 foot climb.  The first three or so miles of the hike is on a maintained forest road through open, old forest. The remainder is the steepest and roughest part of the hike, with big tree fall and some cross country travel.  Your reward for taking on the challenge is a quiet, open summit ringed by old growth trees.  Drive time from Portland is about 80 minutes across the Hood River toll bridge.

Lava Butte is closed to vehicles in the winter, but open for hiking. You can park at the closed visitor center, or there's an option to pull off 97 near where the Lava Butte road passes the highway. From here there's a very short trail through the brush and you're on the road. We did this option which puts the hike at about 1.2 mi and 540' gain. 

The road was mostly clear of snow and ice, with just a handful of spots that had it. We did not need the microspikes we brought in our packs, but had the temps been colder, they would've been neccessary in some spots. 

Overview

For this activation, I followed the recommendation made by N7LF in

Hershberger is a lovely little lookout with a great 360 view, Crater Rim, Rabbit Ears, etc. I went when it was very hot, after I did a difficult hike up Weaver Mountain. The lookout is just in the AZ and I took advantage of a bit of shelter from the sun and the rails to erect my mast. Poor data service at the LO but I think I had service if I walked a little ways away from it.

Two years late with summary so from foggy memory... Mount Stella was a straight forward hike up a blocked road. There is an old wooden lookout at the top. I did this on my way home from doing Mt. Scott and Dutton in CLNP with K7ATN and WW7D. If I recall correctly there is zero data service as this was not on my original agenda and I could not spot or do an alert. Luckily ATN and Darryl were still near and there were a group of hams contracted for communication repair at a fire lookout up north that could copy me also on my 2m HT. Plenty of room to set up.

This is an alternate summit route to what W6PZA wrote up here:  http://www.pnwsota.org/blog/w6pza/2020-november-30/summit-4420-or-november-2020 .  You can take the Cole Loop Trail 854 that crosses the road near the second gate on the road going up to Gray Butte.

Desert Cone by Mike-NS1TA.  About 2.5 miles OW and 700 feet gain.

Standard Mt. Hood disclaimer: conditions vary by the hour, experience interpreting conditions and forecasts are essential for safe alpine travel.

There are several good trip reports that outline the route and condition aspects of this trip, so I'll try to stick to what was specific about this activation.

The 5140 summit is a pleasant one mile hike from FR-2610 in the Ochoco National Forest. The turnoff to FR-2610 is right off of Hwy 26 and about 22 miles East of Prineville.  I activated in the winter on snow shoes, I found a road bed for the hike up that may allow a near drive up in the summer.

This is my 3rd winter activation this year on W7I/ER-054, Red Mountain. It was a great ski tour and a successful activation. I made a short video to show what it's like to do a ski tour activation in the winter in Teton Valley Idaho. Lesson Learned: The skiing is much better in January than in March.

https://vimeo.com/791703045