Soak wooden skewers in water for 30 minutes if using.
Parboil acorn squash cubes for 4 to 5 minutes until just barely tender. Drain and pat dry.
Toss venison and squash separately with olive oil, rosemary, garlic powder, salt, and pepper.
Thread venison and squash onto skewers, alternating pieces.
Sear skewers in hot olive oil for 2 to 3 minutes per side, about 8 to 10 minutes total, until venison reaches 130 to 135°F and squash is caramelized.
Rest skewers 3 to 5 minutes.
Off heat, stir butter, balsamic vinegar, and honey into the skillet to make a glaze. Drizzle over skewers before serving.