This is my favorite (although not the healthiest) way to prepare acorn squash. Normally, I'd puree it in a soup (with earthy fall flavors like bacon, chipotle, cumin, or roasted garlic) but for this recipe I decided to highlight the maple flavor, turning the puree into a milkshake. Coconut milk adds richness, vanilla rounds out the flavors and signals "dessert". —offtrailcuisine
With a very sharp knife, cut the squash in half. Cut off as little as possible from each small end, just so that each half sits flat.
Scrape the seeds and strings out of each half. Try not to pierce all the way through the squash. Place on a foil lined baking sheet.
If you'd like, you can clean off the seeds, then roast them in your 400 degree oven for a snack while your squash cooks. Spread on a cookie sheet, drizzle with olive oil, season with lots of salt and pepper, and roast until golden brown.
Combine the butter and 1/4 cup maple syrup in a medium bowl or glass. Microwave on "high" until the butter is melted, about two minutes. Stir to combine
Pour 1/2 of the butter/ syrup mixture into each squash cavity (this is why you didn't want to pierce through them in step 2, so the liquid doesn't drain out). Spoon liquid onto the cut surfaces of each half, coating generously.
Roast, uncovered, until a fork very easily penetrates deep into the squash flesh, about 1 hour and 15 minutes.
Remove from the oven (being careful not to spill) and cool. Pour the liquid in the cavities into a large bowl or pot. Scoop out the flesh and add it to the liquid.
Add the coconut milk and vanilla to the squash mixture. Puree with a blender or immersion blender. Add 3 tablespoons maple syrup or to taste (since a variable amount of the liquid will leak or spill each time, this step has some wiggle room. You should taste a distinct maple flavor and plenty of sweetness (remember, it's dessert!) without being cloying). Blend until well combined and extremely smooth.
Chill until very cold (I chilled overnight). Serve in a glass with a thick straw.