OCSR
The Oregon Crest Ski Route is not a trail, but a route across the state inspired by the Pacific Crest Trail. It is too dangerous to ski the PCT in all places, so this route aims for safety while remaining as close as possible.
Purple is the route I took with a few fixes made by hindsight (I wish I would have gone that way!). Light blue is alternates that I may or may not have tested myself. Take everything as only a suggestion!! Modify your micronavigation according to conditions! Also realize that some segments will make sense from the south but not from the north, or from approaching by uphill or downhill.
Structures, such as outhouses, cabins, and bridges may be locked, buried, or otherwise unavailable.
Please share your experiences so I can improve the map!

Main route

Govt Camp to Cascade Locks

Santiam Pass to Govt Camp
This segment is a mix of super easy forest roads, glorious views of Hood and Jefferson, and dangerous mountaineering sections. Between forest road 2243 and Breitenbush Lake you will have poor to dangerous conditions. There is a quarter mile chute with steep narrow sides you must traverse without falling in the creek. There are steep hillsides requiring you to ascend/descend on all fours. Winds at Park Ridge knocked me over. The north face can be steep and icy. West and south of Jefferson Peak has lots of steep ridges with streams at the bottom. Three spring attempts have all failed. If a route without any road walking is to be found, it will need to be during winter.
The Salmon Huckleberry Wilderness between Clear Lake and Govt Camp is year round marsh cut by flowing streams. I know of no way through it, yet. Thus, the road walk on Hwy 26. Again, early to mid winter appears to be the only possible time to traverse the wilderness.
However, Timothy Lake sits near 3000 feet so its snow season is short and usually starts late.
Therefore, to successfully complete this segment, you need to start late enough when there is sufficient snow at Timothy Lake, but early enough that it is still cold to get around Jefferson!

Elk Lake to Santiam Pass

Crescent Lake to Elk Lake

Diamond Lake to Crescent Lake

Hwy 62 to Diamond Lake

Hwy 140 to Hwy62

Hwy 66 to Hwy 140

Hwy 99 to Hwy 66

Mt. Ashland road

Cabin to Mt Ashland

Structures

outhouse

cabin

town

broken shack

lodge

storage barn

gas station

Log
The log is 30 feet downstream (west) of the narrow part. The south end of the log is braced up in a folded tree trunk to hopefully make it easier to use in deep snow.
There are 4 possible ways to cross Mesa Creek. Approach them by the PCT or my alternate to the west so you can avoid the thicket due north of the middle crossing.

bridge

Log
The PCT has a split log bridge low to the water. It might be too low to easily access.
There are 4 possible ways to cross Mesa Creek. Approach them by the PCT or my alternate to the west so you can avoid the thicket due north of the middle crossing.

log
log and branches collected a couple feet of snow that allowed me to venture about 5 feet towards the other side where I could grab a small tree. I took off one ski and promptly stepped through the snow and saw the water below! Only 6 inches deep, but wet and cold!!
There are 4 possible ways to cross Mesa Creek. Approach them by the PCT or my alternate to the west so you can avoid the thicket due north of the middle crossing.

Lodge
Timberline Lodge
http://www.timberlinelodge.com/

shelter

shelter
Warming hut in plowed parking lot. Nearby restrooms.

Big Lake camp
Big Lake Youth Camp
http://biglake.org/pct-hikers/
They have a PCT welcome center just for hikers, and now skiers!

outhouse
not verified

hatchery

Lodge
Hoodo ski lodge
https://skihoodoo.com/

Lodge
Willamette Pass Ski Lodge
http://www.willamettepass.com/

observatory

cabin
Maiden Peak Cabin

cabin
Backcountry ski patrol cabin
https://sites.google.com/view/wbpsnow/home

shelter
Gold Lake Shelter
Coordinates from USFS website

Mt. Bachelor ski lodge

Elk Lake Resort
http://elklakeresort.net
open in winter

warming hut
Part of Mt. Bachelor's nordic ski area. Had gas heater working during the day. No outhouse or water.

resort
Lemolo Lake Resort

Shelter Cove Resort
Store is closed in winter, but the lodge is open year round
https://highwaywestvacations.com/properties/sheltercove

store
Small but well stocked store with two tables to sit at and relax. Motels across the road.

outhouse
Nearby Crescent Lake Resort is closed in winter, but there is talk of changing that.
http://crescentlakeresort.com/

Diamond Lake Resort
http://www.diamondlake.net

Timpanagos Lake shelter

hut
This is a popular, groomed sno-park for snow mobiles. Could be crowded. No overnight camping allowed, but a good wood stove with a storage room full of firewood is available. Two outhouses nearby.

The door of the outhouse at Cold Spring trailhead faces south and has a protected entryway so this should be accessible all winter long.

There are two vault outhouses that face west to the driveway and parking lot which are plowed, so the doors will probably open. There is also a big empty lodge-like structure that you can dry out in.

lodge
Rim Village and Crater Lake Lodge fast food, bathrooms, gift store
https://www.nps.gov/crla/planyourvisit/visitorcenters.htm
outside bathrooms are heated, have running water and flush toilets, and are always left open

HQ
Offices and bathrooms are open only during the day

Lake of the Woods Resort
https://lakeofthewoodsresort.com/

Hyatt Lake Resort
http://hyattlake.com

Shelter
Grouse Gap Shelter. Two walled shelter with nearby outhouse

Shelter?
Wrangle Campground. Rundown. Outhouse?

Callahan's Lodge
http://callahanslodge.com/

Cabin
no water or restroom, wood stove, porch

Mt. Ashland Ski Lodge
https://www.mtashland.com/

Dutchman Peak Lookout

Callahans Lodge

three sided shelter with roof made of piled rocks and loosely laid boards

tunnel
About 10 feet wide and high under the highway. Looks like good protection!

Piped spring

Lodge with porch

pavilion and outhouses

lodge
Mazama village

Alternates

Maiden peak cabin

Skyline alternate