Save It The oven was still warm from baking bread when I spotted two acorn squash sitting on the counter, forgotten from the farmers market haul. I had a pot of leftover chili mac on the stove and suddenly thought, why not marry the two? That spontaneous decision turned into one of those meals where everyone went quiet for the first few bites, then asked for seconds. The drizzle of hot honey was a last-minute gamble that paid off beautifully.
I made this for a small dinner party on a chilly October evening, and the presentation alone had everyone reaching for their phones. Cutting into the stuffed squash released a cloud of steam scented with cumin and smoked paprika. My friend who claimed she did not like squash ended up scraping her bowl clean and texting me for the recipe before she even left.
Ingredients
- Acorn squash: Choose squash that feel heavy for their size with firm, unblemished skin, and remember they become incredibly sweet and tender when roasted cut side down.
- Olive oil: Brushing it on the squash before roasting creates a caramelized edge that adds depth to every bite.
- Yellow onion: Dicing it finely helps it melt into the chili mac, building a savory base without chunks that overpower the texture.
- Garlic: Fresh cloves minced at the last second release the most fragrance and prevent that bitter, burnt taste.
- Red bell pepper: It adds a pop of sweetness and color that balances the heat from the spices and jalapeño.
- Jalapeño: Seeding it tames the fire while keeping a gentle warmth, but leave the seeds in if you crave more kick.
- Black beans: Rinsing them well removes excess sodium and that slightly metallic canned taste.
- Diced tomatoes: Use the kind with juices included because that liquid helps cook the pasta and builds a saucy consistency.
- Tomato paste: A tablespoon intensifies the tomato flavor and thickens the mixture so it clings to the macaroni.
- Elbow macaroni: The small curved shape traps all the chili goodness and cooks perfectly in the skillet without needing a separate pot.
- Vegetable broth: It infuses the pasta with flavor as it simmers, making every piece taste seasoned from the inside out.
- Chili powder: This is your main spice, so use a fresh jar for the best warmth and complexity.
- Smoked paprika: It whispers campfire and depth into the dish without adding heat.
- Cumin: Earthy and essential, it pulls all the southwestern flavors together.
- Dried oregano: A pinch adds an herbal note that brightens the tomato base.
- Cheddar cheese: Sharp cheddar melts beautifully and adds a creamy, tangy richness that balances the spice.
- Honey: The base of your hot honey drizzle, it caramelizes slightly and clings to the squash in the best way.
- Hot sauce: Start with less and taste as you go, because the heat builds and you can always add more.
- Cilantro: Fresh and bright, it cuts through the richness right before serving.
- Green onions: Sliced thin, they add a mild bite and a splash of color on top.
Instructions
- Prep the squash:
- Preheat your oven to 400°F and line a baking sheet with parchment to prevent sticking. Brush the cut sides of your halved, seeded squash with olive oil, season with salt and pepper, then lay them cut side down so the flesh caramelizes beautifully.
- Roast until tender:
- Slide the baking sheet into the oven and roast for 35 to 40 minutes, until a fork glides through the flesh like butter. The edges will turn golden and the natural sugars will concentrate into something almost candy-like.
- Start the chili mac base:
- While the squash roasts, heat a tablespoon of olive oil in a large skillet over medium heat and toss in your diced onion. Sauté for 3 to 4 minutes, stirring occasionally, until it softens and turns translucent.
- Build the flavor:
- Add the minced garlic, diced bell pepper, and jalapeño if you are using it, cooking for another 2 to 3 minutes until fragrant. The kitchen will start to smell incredible at this point.
- Add the hearty ingredients:
- Stir in black beans, diced tomatoes with their juices, tomato paste, uncooked macaroni, vegetable broth, chili powder, smoked paprika, cumin, oregano, and salt. Bring everything to a boil, then lower the heat to a gentle simmer.
- Simmer the mac:
- Cover the skillet and let it cook for 10 to 12 minutes, stirring now and then to prevent sticking, until the macaroni is al dente and most of the liquid has been absorbed. The pasta should be tender but still have a little bite.
- Stir in the cheese:
- Remove the skillet from the heat and fold in about two thirds of the shredded cheddar, stirring until it melts into a creamy, cohesive filling. Save the rest for topping.
- Make the hot honey:
- In a small bowl, whisk together the honey and hot sauce, tasting as you go to get the heat level just right. It should be sweet with a slow building warmth.
- Stuff the squash:
- Once the squash halves are roasted, carefully flip them upright on the baking sheet and spoon the chili mac generously into each cavity. Sprinkle the remaining cheese over the top.
- Melt the topping:
- Return the stuffed squash to the oven for 8 to 10 minutes, just until the cheese is melted, bubbly, and starting to brown in spots. Keep an eye on them so the edges do not burn.
- Finish and serve:
- Drizzle the hot honey over each stuffed squash half, letting it pool in the crevices and glaze the top. Garnish with chopped cilantro and sliced green onions, then serve immediately while everything is hot and gooey.
Save It There is something magical about serving this dish on a cool evening when the windows fog up and everyone gathers around the table. The combination of textures, the way the sweetness plays against the spice, and that glossy hot honey finish make it feel special without being fussy. It became the kind of recipe I pull out when I want to impress without stressing, because it always delivers.
Making It Your Own
If you want a heartier version, brown 8 ounces of ground turkey or beef with the onions and let it mingle with the beans and tomatoes. For a vegan spin, swap in plant-based cheese and use maple syrup instead of honey for the drizzle. I have also tried butternut squash when acorn was not available, and it worked beautifully, just adjust the roasting time since butternut can cook a bit faster depending on size.
Storing and Reheating
Leftovers keep well in an airtight container in the fridge for up to three days, and I have found they taste even better the next day after the flavors meld. Reheat individual portions in the oven at 350°F for about 15 minutes, covered with foil to prevent drying out, or microwave gently with a splash of broth to loosen the filling. The hot honey can be made ahead and stored in a jar at room temperature for up to a week.
Pairing and Serving Ideas
This dish stands strong on its own, but a crisp green salad with a tangy vinaigrette cuts through the richness beautifully. I have also served it alongside warm cornbread or tortilla chips for scooping up any chili mac that escapes the squash bowl. A cold beer or a lightly chilled rosé pairs surprisingly well with the sweet and spicy contrast.
- Try crumbled cotija or feta on top for a salty, creamy finish.
- Add a squeeze of fresh lime juice right before serving to brighten everything up.
- If you love crunch, sprinkle crushed tortilla chips over the cheese before the final bake.
Save It This recipe has earned a permanent spot in my fall and winter rotation, and I hope it becomes one of your favorites too. Enjoy every sweet, spicy, cheesy bite.
Recipe FAQs
- → Can I make this dish vegan?
Yes, substitute plant-based cheese for the cheddar and replace the honey with maple syrup or agave nectar. The rest of the ingredients are naturally plant-based.
- → What other squash varieties work well?
Delicata squash and butternut squash both work beautifully. Delicata requires less roasting time due to its smaller size, while butternut may need a few extra minutes in the oven.
- → How spicy is this dish?
The heat level is adjustable. The jalapeño adds mild to moderate spice, while the hot honey drizzle provides a customizable kick. Start with 1 teaspoon of hot sauce and increase to your preference.
- → Can I prepare the components ahead?
Roast the squash and prepare the chili mac filling up to a day in advance. Store separately in the refrigerator, then stuff and reheat in a 350°F oven for 15-20 minutes before serving. Add the hot honey just before eating.
- → What sides pair well with this main?
A crisp green salad with citrus vinaigrette cuts through the richness, while cornbread complements the Southwestern flavors. Roasted vegetables or sautéed greens also make excellent accompaniments.
- → Can I add meat to this dish?
Absolutely. Brown 8 oz of ground turkey or beef with the onions in step 3. The meat adds extra protein and heartiness while maintaining the dish's flavor profile.