The Pine Creek Trail is the easiest way to reach the summit meadow of Baldy Mountain. Bushwhacking routes are readily available and you may choose to take this route, but the trail offers a nice steady grade that is not terribly demanding and is quick.
If you're proficient at snowshoeing, I would say Baldy has outstanding snowshoe potential. The road is easy to follow, and the summit meadow is large enough and extremely visible so route-finding would be simple at worst. For the cross-country skier the summit of Baldy is very long (over a mile) and extends to the base of Pine Creek Mountain to the south.
Strawberry Mountain from Pine Creek Trail
Travel five miles east of John Day on highway 26 and turn right onto Pine Creek Road (US 5401). Follow this road 8.5 miles to the Pine Creek Campground where you will want to park unless you have a four wheel drive vehicle. The trailhead is only half a mile further up the road (go left at the Y just pass the campground), so this campground makes a good place to park. To avoid getting lost on the drive in make sure to follow the most maintained road and always take the road that goes up when you come to any splits as there are several roads that spur off of Pine Creek Road.
The Pine Creek Trail is a mild switchbacking climb up the face of Baldy Mountain. Before hitting the first switchback you will cross over the West Fork of Little Indian Creek. If you are going to find water on this hike it will be here, if the creek is dry, dont count on there being water. Shortly after crossing the creek, you will begin a series of switchbacks that will eventually bring you to the edge of the summit meadow west of the saddle that runs north south across Baldy. During these switchbacks you will cross Little Indian Creek several times. At no point is there a bridge so be prepared to ford the meager stream pictured below.
Once through the switchbacks and at the edge of the summit meadow you can follow the trail towards the saddle and the mountain summit on the other side; or directly cut up the mountain if you would like to hit Baldy's west summit along the way. The remains of an old road, barely discernable runs the length of Baldy's summit meadow, this can be followed between the main and west summits if you desire.
Finally, during the spring of 06' there was a Powerade bottle hidden in the summit cairn serving as a summit register. Be sure to add your name!
This is a short hike, less than 3 miles with a very accessible grade so my only recommendation is water beyond the obvious requirements.
Many locals say cougars are prevalent in this area, so keep that in mind if your hiking with children or pets.