Very few trails can boast the steepness and elevation gain of Boulder Ridge outside of major glaciated mountains. The result of your hard work, however, will reward you with one of the best possible views of Mount Hood in all the valley. Despite such an incredible view, you are likely to enjoy the peace and quiet of being alone on the trail.
The trail begins on the west side of the river. Getting there is a simple matter of following the signs and navigating through Wildwood Park. You will reach a sign that designates the beginning of Boulder Ridge. It is unmistakable because you will see the trail begin to climb the hillside to the left. The beginning of the trail appears relatively rugged and slippery, but don't be dismayed, it is short, and definitely better afterward. The trail follows many switchbacks as you climb, climb and climb in elevation toward the ridge. Look for opportunities to find viewpoints to see the valley and Mount Hood. There are a few small stream crossings along the way that were a nonissue in September but could pose a problem to non-waterproof footwear during the winter or spring runoff. You will forget about the highway noise below as you reach the ridge. The forested landscape becomes quiet, and you are left with your thoughts. There are no branches for the entirety of the trail to Huckleberry, so do not worry about which way to go. At one time there was a "Plaza Trail," as you will see from the sign, but the entrance of Plaza Trail to the junction of the Boulder Trail is all but grown over and nonexistent. The Boulder Trail merges with Plaza at the sign and continues on to Huckleberry Mountain. There won't be another junction until after the summit when the Plaza Trail joins Bonanza. Enjoy the views as you continue along the ridge steadily gaining elevation.
The first clearing offers the best view of the valley and Mount Hood, but there are a few more clearings as you continue on to the true summit. The survey marker designating the summit is difficult to find, so you may have to rely on a GPS to guide you to the summit.
After you have basked in the glorious views of Mount Hood, there are two options: