Mount Ashwabay is organized into a modern stacked-loop trail system design, in which the closest trails to the trailhead are the easiest (perfect for beginners), the next trails are intermediate-friendly, and then off of the longer intermediate you can access more advanced black-diamond lines.

The route shown here is the best way to maximize the mileage at Ashwabay, creating an impressive 17-mile loop through the network. However, this route does incorporate the most advanced trails at Ashwabay. If you skip the more difficult trails of Lady Slipper and Trogdor, you can reduce the difficulty of this ride from "Difficult" to "Moderate." And if you simply opt to pedal Diesel Bear, that would rank as an "Easy" ride on the FATMAP Difficulty scale.

The ride begins on the easy Diesel Bear trail, which gradually climbs up the hillside into the trail system. After reaching the major trail junction where a plethora of different trails come together, the climb kicks up steeply on the Trogdor Trail to gain the top of Mount Ashwabay. Here you'll enjoy expansive views over Northern Wisconsin and the Apostle Islands out in Lake Superior. Take a few minutes to enjoy the view, but know that your ride is far from over!

The descent off the top of the mountain will start to give you a sense of what's in store for the rest of the ride, with plenty of chunky rock gardens, a few ledge drops, and some low berms to rail.

After dropping out of Trogodor, you'll continue taking right turns to hit Hoot 'n' Hollow and Lady Slipper. Both of these trails are cut from the same cloth... er, rocks. You'll encounter punchy climbs followed by gnar-flow descents. That said, Lady Slipper is definitely the most challenging trail in the system, with a few lines offering A and B options. The A options reach black diamond difficulty, but only temporarily, thanks to a few fair-sized ledge drops and double jumps. You'll also bash through plenty of expertly-placed rocks on this raucous downhill!

Once done with Lady Slipper, you'll pick up the lengthy Tsuga Daddy loop, riding it in a clockwise direction. The trail character changes here, with the technicality easing up dramatically. Tsuga Daddy allows you to just put your head down and pedal, railing through about 5 miles of fast singletrack and low berms. You can make the trail a bit more difficult by hitting the optional kickers and hucking off the sharp, steep rollers.

After finishing Tsuga Daddy, there's a bit more easy pedaling on Hot Saw before the final flowy descent on Dirt Lip and Diesel Bear to drop back to the trailhead where you began.

Sources: https://www.mtashwabay.org/mountain-biking.html