The dandelion is in fluff phase, and there is a pixie holding onto a seed. He explains, "We can magically make ourselves light enough to be carried on the wind, if it's going in the right direction. I only need a gust to the east, so of course there's a steady southwest breeze."
The dandelion itself is thick and strong enough to climb. But if you were to fly away on the wind, you probably couldn't get back, so there's no point in spending the energy to go up the stem. Trails converge here from the west, southwest, and southeast.