The first night: big climbs in the dark on fresh legs
You start at 6 PM, and within the first stretch the course throws you at the big climbs while it is getting dark. The long haul up toward Elliott Knob, one of the highest points in the area, is the kind of grind that sets the tone for the whole race. This is where Grindstone is quietly won or lost, because it feels easy in the cool evening air on fresh legs and it is so tempting to push. Hike the steep pitches efficiently, keep your effort honest, and let faster people go. The first night is a setup, not a race.
Run by headlamp the way you practiced, eat on a schedule even though you are not hungry in the dark, and stay on top of your layers as the ridges get cold. Get to sunrise with your legs and your stomach intact and you have done the single most important thing in this race.