Many choose the more relaxed out-and-back route along the Crooked River Trail, from where they can already catch an extraordinary glimpse of the natural spectacle. But if you want to experience Smith Rock to the fullest, you can’t avoid the steep climb at the beginning of the Misery Ridge Trail. On the back side of the highest point at Smith Rock is Monkey Face, a rock pillar popular with climbers. Below Monkey Face, the trail forks. If you want to take the shorter route along the Crooked River, you should now keep left along the Mesa Verde Trail. Turn right to reach the Summit Trail, or alternatively, turn right when you reach the end of the Mesa Verde Trail at the river. The Summit Trail goes around Smith Rock on the right, again going uphill about 920 feet coming from the river. Since the Summit Trail can only be accessed by steeper grades, it is usually less busy than the River Trail, but it is also longer. The Misery Ridge + River Trail is 3.5 miles long and can be accomplished in just over two hours. It took me almost three hours to walk and take pictures. The Misery Ridge + Summit Trail has a length of about 6 miles and takes about 3.5-4 hours. Both offer great views of the landscape, plant and biodiversity at Smith Rock. In the background, you can see the snow-capped peaks of Three Sisters, Mount Jefferson and Mount Hood, while Canada geese and otters swim in the Crooked River and hawks, ospreys, and bald eagles glide in large dark shadows along the cliff faces of Smith Rock.
Here you can find more information about Smith Rock State Park.
If you want to come in a suitable outfit, you will surely find it here.
And here you can book a guided 1.5 hour horseback ride from a private ranch.