The original trail system in the Ashland Watershed was created by mountain bikers over 30 years ago. The system included trails with names themed after Lewis Carroll’s novel “Alice in Wonderland” with names like Alice in Wonderland, Cheshire Cat, Rabbit Hole, Queen of Hearts, White Rabbit, Caterpillar, and March Hare. Most are still in use today. However, none were constructed with the approval of the US Forest Service and were considered “rogue” trails. With trail running increasing in popularity, the trails became crowded causing conflicts between the bikers and runners/walkers and equestrians. Around 2008 a group called the Ashland Woodlands & Trails Association (AWTA) was formed. The group was comprised of runners, walkers, and bikers, with input from local equestrians. Their goal was to reduce conflicts between trail users and create a sustainable trail system in the Ashland Watershed.  Pick up a map and create your own fun route. There are many options within walking distance from the Plaza.

Park Street Entrance

Anne’s favorite Ashland Watershed trail runs


Anne Crispino-Taylor started trail running while living in Ashland and here are some of her favorite routes.


Park Street  (Oredson Todd Woods)

One of my favorite routes starts at the top of Park Street, about a quarter-mile south of SOU off Siskiyou Blvd. Take White Rabbit to Caterpillar. Double back on White Rabbit to Mike Uthoff and return to Park Street for about six miles. Add the Lewis Loops (Gyre and Gimble) for another four miles.

For a 30-mile out and back run head up White Rabbit, to Caterpillar, to Toothpick, and up Catwalk to Four Corners. From Four Corners go up FS Road 2080-200 to Bull Gap and on up to Mt. Ashland.



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Fairy Ponds Trailhead

A nice out and back from the Fairy Ponds includes Lower Wonder to Wonder to 2060 and back to the Fairy ponds for about six miles.

Another good trail run from the Fairy Ponds includes Bander to Red Queen to Caterpillar to the White Rabbit parking area, and down Alice back to Bander – about seven miles.

Also from the Fairy Ponds go up 2060 to Horn Gap to No Candies (short for No Candy Asses), to FS Road 2060-400 to 2060, and back down for 18 miles.

Madrone Trees in the Ashland Watershed

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