Welldiggers Ass is a very good peak to have a winter destination. There are many good reasons to pick Welldiggers Ass as a good winter hiking destination. The biggest reason is that despite the summit being forested, good views off to the south from the summit area as well as good views off to the north can be seen from hike up Welldiggers Ass. The peak is also relatively safe from avalanche danger in that there are no exposed slope great than 15% degrees on route to the summit. The peak does not require an ice axe and bringing an ice axe would just be dead weight. The peak is also very easily accessible from Route 2 miles east of the Stevens Pass ski area.
The main route to the summit follows a number of snowed in gravel roads. Follow the gravel roads which are usually well marked by skiers all the way up to near the ridgeline. From go off travel and traverse to the east as you rise. You should quickly hit an open area where Welldiggers Ass and its burnt out forest will lie to the east. From there traverse along the east over to the summit ridge. Head up the summit ridge and as it first enters the burnt out area and then heads to the very true summit. The very true summit sits right in the middle the ridge although the views lie to the east. Views south and east include Middle and North Chiwaukum, Arrowhead and many, many others in the region.
It should be noted that I recommend Welldiggers Ass to many first time winter hikers and snowshoes. There is very little in technical difficult and the risks of Avalanche Danger and highly exposed slope is minimal add on that it is only 5 miles roundtrip and 1500 feet of elevation gain and Welldiggers Ass become a very viable options if roads in Stevens Pass are clear.
Getting ThereVIA STEVENS PASS: Take Route 2 to two miles east Stevens Pass. Stevens Pass is located 20 miles east of Skyomish and 30 miles west of Leavenworth. You want to park in Stevens Pass Ski Area overflow lot on your south side 2 miles east of the main ski area. There will be a building that is marked no tresspassing and no parking to the right of the building. That is residence for the workers of the ski area. The large parking to the left is the overflow and is legal to park there. From there you want to go to the right of the building where you will pick up the route to the summit of Welldiggers Ass.
Red TapeProvided you park in the ski resort overflow lot on the south side of US 2, there will be no fee.
CampingWelldiggers Ass is not recommended for camping due to the mountain only being 6 miles roundtrip. In my research though I did not see any signs preventing one from camping. If possible camp out on the summit, which has views around it, yet has enough trees to bring cover from any serious elements.
Weather LinksHere is a link to shots of live shots of Stevens Pass.
Here is the NOAA forecast for the western Cascades