In my opinion, every road runner at some point in their running "career" should try out a trail race. The Bandersnatch 5k trail race in Ashland is a great little race in Southern Oregon to get a taste for a hilly trail. This year's event takes place on Saturday, November 19th, with an 8am start in Lithia Park. From there runners take a paved road and fire road into the park before turning onto the Bandersnatch single track trail, and on the first half of the course will have to climb an elevation gain of 800ft. A lot of the climbing (and descending) will be on switchbacks, so don't expect to be very fast, but the views at the top are breathtaking.
Course Map (click to enlarge)
While the first half of the course is all uphill, you can make up some time on the downhill second half. The course has a time limit of 1h15min, which averages out to around 25 minutes per mile. At the finish, each participant will receive an event trucker hat and refreshments. As you arrive at the park, please be sure to park in legal parking spots only without blocking gates or obstructing other visitors.