Squash is hands down one of my favorite side dishes to make in the fall and winter. Squash in all varieties is such a versatile veggie that roasts beautifully and makes a hearty and satisfying accompaniment to a good protein like a thick bone-in pork chop or a nice steak.
This roasted acorn squash has a delicious caramelized maple crust that packs some heat. I love spicy food and this is one of those unique side dishes that hits all the best flavor profiles. The caramelized maple syrup really brings out the sweetness of the roasted squash and helps to balance out the cayenne.
This side dish does take some time in the oven but the prep work couldn’t be easier! It is an impressive and easy side dish to serve when hosting a dinner party. I like to prep the acorn squash the night before to save me time before guests arrive.
To prep the squash in advance, cut in half through the stem and tip (see tip below) and scoop out the seeds. Drizzle the oil and seasoning mix over each squash and store them on your parchment or foil lined baking sheet. Cover tightly with plastic wrap and refrigerate over night. Pull the sheet pan out of the fridge 20 minutes before baking (step 4) and then continue with the remainder of the cooking instructions.
Cooking “Life Hack”: Pick up a rotisserie chicken at your local grocery store (I think Central Market and Whole Foods have the best quality rotisserie chicken in my area). Serve the acorn squash alongside a piece of rotisserie chicken and a quick side salad for an easy, healthy, and satisfying weeknight meal.
Tip: If you’re nervous about cutting through the hard squash poke holes along the line you will cut. Microwave each acorn squash for 3 minutes. Hold the squash with a kitchen towel to halve each acorn squash. This will make the skin and flesh a little easier to slice through.
Tip: This dish packs a lot of heat. When I am preparing this for my family I omit the cayenne pepper on the two pieces of squash I serve to my kids as my 11 month old is still very much a messy eater and rubs food in her eyes.
- 2 large acorn squash halved, seeds removed
- 2 tbsp olive oil butter will work also
- 1 pinch cayenne a little goes a long way
- 2 tbsp brown sugar light or dark
- 1 tsp flaky sea salt
- 4 tbsp maple syrup
- 3 tbsp raisins optional
- Preheat oven to 400*.
- Line a baking sheet with foil or parchment paper. Place acorn squash cut side up on the lined baking sheet and drizzle the olive oil all over the flesh of the squash.
- Mix the cayenne, brown sugar and salt together and sprinkle it all over each acorn squash half. (You will likely not need all of the seasoning mix).
- Roast at 400* for 45 minutes.
- Remove from the oven. Test the squash to make sure it pierces easily and is fork tender. (Each acorn squash will vary in size, some may take an additional 10 minutes or so.)
- Drizzle each acorn squash half with maple syrup and sprinkle raisins inside each squash cavity (if using).
- Return squash to the oven and bake an additional 10 minutes.
I love seeing photos when you make my recipes! Make sure to tag me @katyscookin on Instagram when you make this Spicy Maple Glazed Acorn Squash. Thanks for stopping by!