Preheat oven to 400°F (200°C). Line a baking sheet with parchment paper.
Carefully cut each acorn squash in half from stem to stern. Scoop out seeds and pulp.
In a mixing bowl, whisk together maple syrup, olive oil, apple cider vinegar, salt, and pepper.
Brush the cut sides of the squash halves generously with the maple glaze.
Place the squash halves cut-side up on the prepared baking sheet.
Roast for 30 minutes.
Remove from oven and baste with remaining glaze.
Return to oven and roast for another 15-20 minutes, or until tender and caramelized (fork easily pierces the squash).
Broil for 2-3 minutes for even deeper color (optional).
Garnish with chopped nuts and herbs before serving.