There are a lot of good trails out of this area, assuming there's enough snow this winter to make it worthwhile. What the dry eastern air giveth (powdery snow) it taketh away (as soon as it warms up a little).
Naneum Meadows is one of several destinations for better skiers. Starting from the Swauk Pass Sno-Park, there is a way to shorten the trip (but not the elevation gain) by leaving road 9716 at its intersection with spur 141, heading SSE to a saddle between Diamond Head and its neighboring peak to the east. Bear in mind this is an avalanche chute, so test the snow before you go up.
Cross road 9712 and continue south to Naneum Meadows. From the meadows, use trail 1389 and road 35 to reach Lion Rock CG, excellent camping about 10 miles in. Or choose one of the many loop opportunities, including via Haney Meadow and Tronson Meadow.
Stats: 5 miles, elevation gain 1500', loss 400', high point 5600'.
Getting there: Trail begins at the Swauk Pass Sno-Park, on Hwy. 97.
Note: Requires avalanche knowledge, in addition to route-finding and ski mountaineering skills.