Parking is free, and easy to find in the wintertime, but summertime availability is a different story, with downtown parking getting quite scarce on evenings when the Shakespeare Festival has shows i.e., every night but Monday. Many hotels and B&Bs are located close enough to the center of town to make it an easy walk. There are bike lanes downtown and extending outward from the downtown area, making this an easy town to bike around in.
Most days, the Rogue Valley Transportation District (http://www.rvtd.org) operates buses running from one end of town to the other; these buses are $0.50 for riders remaining within Ashland $2 for those going outside the city limits. Be aware, however, the the buses run limited hours 5:30 a.m. to 7 p.m. and do not run at all on weekends.