Preheat the oven to 400 degrees F. Cut each squash into quarters and scoop out the seeds. Then place the squash pieces on a rimmed baking sheet and drizzle with olive oil. Salt and pepper liberally.
Roast the squash for 40-45 minutes, until fork tender. Meanwhile, dice the pear and mix it with the walnuts, brown sugar, 3/4 teaspoon sea salt, and cumin. Once the squash is tender scoop the pear mixture into the cavity of each squash wedge and top with blue cheese.
Bake again for 10-15 minutes to soften and toast the cheese. Serve warm.