Preheat your oven to 400°F (200°C) and line a baking sheet with parchment paper.

Prepare the pork tenderloin by patting it dry with a paper towel. Sprinkle salt, pepper, minced garlic, dried thyme, and dried rosemary evenly over the tenderloin, pressing the seasonings into the meat.

Heat a tablespoon of olive oil in a large skillet over medium-high heat. Sear the seasoned pork tenderloin on all sides until browned, about 3-4 minutes per side.

Meanwhile, prepare the acorn squash by cutting it in half, removing the seeds, and cutting it into wedges. Place the acorn squash wedges on the prepared baking sheet, drizzle with the remaining tablespoon of olive oil, and season with salt and pepper.

Transfer the seared pork tenderloin to the same baking sheet, nestling it among the acorn squash wedges.

In a small bowl, whisk together the maple syrup, Dijon mustard, and balsamic vinegar to create the glaze.

Brush the glaze over the pork tenderloin and drizzle some over the acorn squash wedges.

Place the baking sheet in the preheated oven and roast for about 25-30 minutes, or until the pork reaches an internal temperature of 145°F (63°C) and the acorn squash is tender and caramelized.

Once cooked, remove the baking sheet from the oven and let the pork rest for a few minutes before slicing.

Serve the sliced roast pork tenderloin with the roasted acorn squash. You can drizzle any remaining glaze over the dish or use it as a dipping sauce.