Even on a cold, gray day in winter, this state park is something to be celebrated. (The last time I was this impressed with a six-mile hike I was in the diverse and mind-blowing landscape known as the South Island of New Zealand.) Smith Rock State Park is stunning and the Misery Ridge Trail is not to be missed.
Once you've paid your $5 day-usage fee in the main parking lot, park and head over to the overlook. From there, you'll follow the switchback dirt path down to the river. Cross the bridge and immediately turn right and then up, following signs marked "Most Difficult."
The initial climb is tough, but once you're at the top, it's smooth sailing. Views of climbers and the surrounding area will impress. You'll soon see the famous Monkey Face, and not wonder how it got its name—it's wonderfully obvious. As you keep descending, you meet up with the Mesa Trail, which takes you along the river and leads you back to the bridge where it all began.
In mid-summer, I've been told this park is filled to the brim with people. In my two hours and six miles in the park in November, I ran into maybe 20 on the trail. I also saw many deer, two coyotes, and a playful (and vocal) river otter.
If you're staying in Bend, don't hesitate to drive the 30 minutes out to Smith Rock to enjoy a lesson in gratitude. Let's hear it for our state parks!