The grades are gentle and at slower speeds, the delightful scenery is more noticeable. At the top, the pleasure of turning around and having gravity as your ally is supreme. Riding uphill can help solve a lot of the problems caused by downhill speed demons. Unlike many single tracks, the Winsor Trail does not require advanced riding skill to negotiate. Much of the trail is smooth and hard packed.
Short sections are steep, have loose rocks or dirt and caution is required.
Other trail hazards include steep drop-offs at trailside, tight turns, and plenty of rocks. When riding downhill, always control your speed. Trail hazards are less pronounced in the uphill direction, but climbing the Winsor Trail will test your stamina. Miles of constant ascent will slowly wear you down. By the halfway point, the air is noticeably thinner than at the trailhead.