The Bear Creek Greenway is the best bet for a longer, all off-road run in the Ashland/Medford area. The paved multi-use trail is also a popular cycle commuting route, as it runs for 20 miles between Ashland and Central Point, passing through Talent, Phoenix, and Medford. Note this is not necessarily the most scenic trail, as it’s sandwiched between Highway 99 and I-5 at the southern end, and runs very near I-5 for much of the way. It is a steady uphill climb headed north.

The southern terminus is in Ashland, at W Nevada St. The first 2 miles follow Bear Creek. It’s 5 miles to Talent, 8 miles to Phoenix, 13 miles to Hawthorne Park in Medford. There are markers every 1/4 mile. This trail map has good information on the trail and segment distances.