Save The first time I saw acorn squash at the farmers market, I had no idea what to do with it. I bought two on a whim, drawn to their dark green ridges and autumn glow. They sat on my counter for three days before I finally decided to roast them and fill them with something warm and hearty. That night, I pulled together a bubbling pot of chili mac with a drizzle of hot honey I'd been hoarding, spooned it into those tender squash halves, and realized I'd stumbled onto something special.
I made this for a small dinner party last fall, and my friend who claimed she didn't like squash went back for seconds. She kept saying it was the creamy, spiced filling that won her over, but I think the squash itself, caramelized and tender from the oven, played a bigger role than she admitted. By the end of the night, everyone was scraping their squash skins clean and asking for the recipe. It became my go to whenever I want something cozy that feels like a hug on a plate.
Ingredients
- Acorn squash: Choose ones that feel heavy for their size with no soft spots, and roasting them cut side down keeps the flesh moist and sweet.
- Olive oil: A good drizzle on the squash before roasting helps the edges caramelize beautifully and keeps everything from sticking.
- Yellow onion: Diced small, it melts into the chili mac and adds a gentle sweetness that balances the spice.
- Garlic: Fresh cloves minced fine release their flavor fast, so add them after the onion softens to avoid burning.
- Red bell pepper: It adds a pop of color and a subtle sweetness that plays nicely with the smoky paprika.
- Jalapeño: Seeding it tames the heat, but if you like it spicy, leave a few seeds in for extra kick.
- Kidney beans and black beans: Together they make the chili hearty and satisfying, plus they hold up well during simmering.
- Diced tomatoes: The canned kind works perfectly here, bringing acidity and moisture to the mix.
- Vegetable broth: It loosens everything up and helps the pasta cook right in the skillet without needing a separate pot.
- Chili powder, cumin, and smoked paprika: This trio builds the warm, smoky backbone of the chili mac and smells incredible as it simmers.
- Hot honey: This is the secret ingredient that ties everything together, a little sweet, a little spicy, and completely addictive.
- Elbow macaroni: It cooks right in the chili, soaking up all the flavors and turning creamy when you stir in the cheese.
- Sharp cheddar cheese: Shredded fresh melts smoothly and adds that rich, tangy creaminess that makes this feel indulgent.
- Fresh cilantro: A handful chopped and scattered on top brightens everything up and adds a fresh contrast to the richness.
Instructions
- Roast the squash:
- Preheat your oven to 400°F and brush the cut sides of the squash with olive oil, then season with salt and pepper. Place them cut side down on a parchment lined baking sheet and roast for 35 to 40 minutes until a fork slides in easily.
- Start the chili base:
- While the squash roasts, heat olive oil in a large skillet over medium heat and add the diced onion, cooking for about 3 minutes until it softens. Stir in the garlic, red bell pepper, and jalapeño, letting them cook for another 4 to 5 minutes until everything smells fragrant and the peppers are tender.
- Build the chili:
- Add the kidney beans, black beans, diced tomatoes, vegetable broth, chili powder, cumin, smoked paprika, salt, pepper, and hot honey, stirring everything together. Bring it to a gentle simmer and let the flavors meld while you move to the next step.
- Cook the pasta in the chili:
- Stir in the elbow macaroni, cover the skillet, and cook for 8 to 10 minutes, stirring occasionally until the pasta is al dente. If it looks too thick, add a splash of broth or water to loosen it up.
- Stir in the cheese:
- Remove the skillet from the heat and stir in the shredded cheddar cheese until it melts into a creamy, luscious sauce. The residual heat does all the work here, so no need to turn the burner back on.
- Stuff the squash:
- Once the squash halves are cool enough to handle, flip them cut side up and spoon generous portions of the chili mac into each one. They should be overflowing with filling, which is exactly what you want.
- Garnish and serve:
- Drizzle extra hot honey over the top and sprinkle with fresh cilantro before bringing them to the table. Serve them hot, with a fork and maybe a little extra napkin.
Save One chilly October evening, I made this for myself after a long day and sat on the couch with the whole stuffed squash in a bowl, scraping out every last bit with my spoon. There was something deeply satisfying about eating straight from the squash, the sweet roasted flesh mixing with the creamy, spicy chili mac. It felt like the kind of meal that didnt need anyone else around to be special, though sharing it always makes it better.
Make It Your Own
If you want to add meat, brown half a pound of ground turkey or beef with the onions before adding the beans and tomatoes, and it turns into a heartier, protein packed version. For extra heat, swap the cheddar for pepper jack or add more jalapeño with the seeds left in. I once stirred in a handful of frozen corn at the end for a little sweetness and crunch, and it was a welcome surprise.
Pairing and Serving
This dish pairs beautifully with a robust Zinfandel that can stand up to the spice, or a light lager if you prefer something more casual and refreshing. I like serving it with a simple side salad dressed in lime and olive oil to cut through the richness. Sometimes I set out extra hot honey and cilantro on the table so everyone can adjust their own bowl to taste.
Storage and Reheating
Leftovers keep well in the fridge for up to three days, though the squash can get a little softer after sitting. I usually reheat individual stuffed halves in the oven at 350°F for about 15 minutes, covered with foil to keep them from drying out. You can also scoop out the filling and squash together, mix them up, and reheat in a skillet for a deconstructed version that tastes just as good.
- Store the stuffed squash in an airtight container or wrap each half tightly in foil.
- If freezing, wrap each half individually and freeze for up to a month, then thaw overnight in the fridge before reheating.
- Add a splash of broth or water when reheating to bring back the creamy texture.
Save This recipe has become one of those dishes I turn to when I want something that feels like home, warm and comforting and just a little bit special. I hope it finds a place in your kitchen, too.
Recipe FAQs
- → Can I prepare the squash ahead of time?
Yes, you can roast the acorn squash halves up to 2 days in advance. Store them covered in the refrigerator and reheat in a 350°F oven for 10 minutes before filling with freshly made chili mac.
- → What can I substitute for hot honey?
Mix regular honey with a few dashes of hot sauce or sriracha to achieve the same sweet-spicy balance. Alternatively, use maple syrup with a pinch of cayenne pepper for a similar effect.
- → How do I prevent the pasta from getting mushy?
Stir the macaroni occasionally while it cooks and check for doneness at 8 minutes. Cook only until al dente, as it will continue softening slightly from residual heat after removing from the stove.
- → Can I use a different type of squash?
Butternut squash halves or delicata squash work wonderfully as alternatives. Adjust roasting time based on size—butternut may need 40-45 minutes, while delicata cooks faster at 25-30 minutes.
- → How should I store and reheat leftovers?
Store the chili mac and squash separately in airtight containers for up to 3 days. Reheat the squash in the oven and warm the chili mac on the stovetop with a splash of broth, then combine before serving.
- → What cheese works best besides cheddar?
Pepper jack adds a tangy, spicy kick, while Monterey Jack offers creamy mildness. For a smoky depth, try smoked gouda. Mix multiple cheeses for even more complex flavor.