Save Last fall, I was staring at two acorn squash on my counter wondering what to do with them when my neighbor mentioned she'd been craving chili mac. Something clicked—what if I stuffed the squash with it? The combination sounded wild at first, but when I drizzled that first batch with hot honey, the sweet-spicy-savory trifecta just sang. Now it's become my go-to dish when I want something that feels both cozy and a little bit fancy.
I made this for a small dinner party in November, and my friend who usually skips anything with beans went back for seconds. She said the squash vessel made her feel like she was eating something special, even though it's basically comfort food. Watching people light up when they realize there's hot honey involved—that's the moment I knew this recipe had staying power.
Ingredients
- Acorn squash (2 medium, halved and seeded): These halves become natural bowls, and their subtle sweetness balances the spicy chili perfectly; choose squash that feel heavy for their size.
- Olive oil (3 tbsp total): Use a good quality one you actually like tasting, since it coats the squash and becomes part of the flavor profile.
- Yellow onion (1 medium, diced): The foundation of your chili mac base; don't skip the caramelization step or you'll miss half the depth.
- Garlic (2 cloves, minced): Fresh garlic makes all the difference here—jarred just won't have the same punch.
- Red bell pepper (1, diced): It adds sweetness and color; I use red instead of green specifically for those flavor notes.
- Jalapeño (1, seeded and minced, optional): This is where you control the heat level; leave the seeds in if you want genuine spice, remove them for just the flavor.
- Black beans (1 can, drained and rinsed): Rinsing them removes the starchy liquid and prevents your filling from getting gummy.
- Diced tomatoes (1 can, 15 oz): Use fire-roasted if your store carries them; it adds a subtle smokiness.
- Tomato paste (1 tbsp): This concentrates the tomato flavor and gives the chili actual body.
- Elbow macaroni (1 cup): Cook it slightly under al dente since it'll finish cooking inside the oven.
- Vegetable broth (2 cups): Low-sodium broth lets you control the salt and prevents the filling from tasting one-note.
- Chili powder, smoked paprika, cumin, dried oregano (1 tsp, 1/2 tsp each): Toast these spices mentally together—they create a warm, slightly smoky backbone.
- Cheddar cheese (1 cup shredded): Freshly shredded melts better than pre-shredded; use sharp cheddar for more personality.
- Honey (1/4 cup): Raw honey has more flavor than processed, and that matters when it's a starring ingredient.
- Hot sauce (1-2 tsp): Choose one you enjoy eating straight; it flavors your entire hot honey drizzle.
- Fresh cilantro (2 tbsp chopped) and green onions (1/4 cup sliced): These garnishes add freshness that cuts through the richness beautifully.
Instructions
- Prep your squash for roasting:
- Preheat your oven to 400°F and line a baking sheet with parchment paper. Brush the cut sides of your halved squash with olive oil and season generously with salt and pepper, then place them cut-side down on the sheet. This positioning lets the flesh caramelize slightly against the hot pan, creating a more complex flavor than if you roasted them skin-side down.
- Start the roasting:
- Slide the squash into the oven for 35 to 40 minutes—you're looking for flesh that yields easily to a fork but isn't collapsing. While they roast, your kitchen will smell like toasted squash and autumn, which is honestly the best kitchen perfume.
- Build your chili mac base:
- Heat olive oil in a large skillet over medium heat, then add your diced onion and let it soften for 3 to 4 minutes until it starts turning translucent. You'll notice the smell change from sharp to almost sweet; that's when you know it's ready for the next step.
- Add aromatics and heat:
- Stir in your minced garlic, diced bell pepper, and jalapeño (if using heat is your thing). Cook for another 2 to 3 minutes until the garlic becomes fragrant and the pepper begins to soften at the edges.
- Build the chili mac filling:
- Add your drained black beans, canned tomatoes with their juices, tomato paste, dry elbow macaroni, vegetable broth, and all your spices—chili powder, smoked paprika, cumin, oregano, and salt. Stir everything together until the spices are evenly distributed and the mixture comes to a boil.
- Simmer until pasta is tender:
- Reduce heat to medium-low, cover the skillet, and let it cook for 10 to 12 minutes, stirring occasionally. You're watching for the macaroni to reach that perfect tender texture and most of the liquid to absorb into the mixture.
- Finish with cheese:
- Remove from heat and stir in two-thirds of your cheddar cheese until it melts completely and coats everything. The filling should be creamy but not soupy at this point.
- Make your hot honey:
- While the filling cooks, whisk together your honey and hot sauce in a small bowl. Start with 1 teaspoon of hot sauce and taste as you go—you can always add more heat, but you can't take it out.
- Assemble the stuffed squash:
- Once your squash halves are tender, carefully flip them upright on your baking sheet. Spoon the chili mac generously into each squash half, letting it pile up naturally, then sprinkle the remaining cheese over the top of each one.
- Final oven finish:
- Return the stuffed squash to the oven for 8 to 10 minutes, just long enough for the cheese to melt into bubbly, golden patches. You'll know it's ready when the cheese looks creamy and slightly browned at the edges.
- Garnish and serve:
- Remove from the oven and immediately drizzle your hot honey over each stuffed squash, then scatter fresh cilantro and green onions across the top. Serve while everything is still steaming and the hot honey is still warm.
Save There's something about a stuffed squash that makes people feel cared for, like you took the extra time to create something thoughtful just for them. That's the real magic of this dish—it's practical enough to be weeknight dinner but special enough to feel like you're doing something memorable.
Scaling This Recipe
If you're cooking for two, halve everything—one large squash split down the middle works beautifully, and you'll have enough chili mac left over for lunch the next day. For a crowd of six or more, I just double the chili mac recipe while keeping two squash per four people; it's easier than multiplying and creating ingredients you don't need.
Making It Your Own
This recipe has natural flexibility built in because the filling and squash are separate until the last minute. Want to add cooked ground turkey or beef for more protein? Stir it in with the onions. Craving it completely vegan? Swap plant-based cheese for the cheddar and use maple syrup instead of honey in your hot drizzle. I've also tested this with butternut squash and it works, though acorn gives you a sturdier bowl.
Storage and Leftovers
This dish reheats surprisingly well because the filling is forgiving and the squash doesn't get mushy a second time around. Store any leftovers in an airtight container in the refrigerator for up to three days, then warm in a 350°F oven for about 15 minutes until heated through.
- Don't drizzle hot honey until you're ready to serve, since it can get absorbed into the filling and lose its impact.
- If you're prepping ahead, you can roast and stuff the squash a few hours early, then just pop it in the oven to reheat and finish with garnish.
- The chili mac filling actually tastes better the next day after the spices have had time to meld, so don't hesitate to make this on a Sunday for Wednesday dinner.
Save This recipe has become something I reach for when I want to cook something that nourishes both my table and my mood. It's the kind of dish that reminds you why cooking at home matters.
Kitchen Help
- → Can I make this stuffed squash ahead of time?
Yes, you can roast the squash and prepare the chili mac up to 2 days in advance. Store them separately in the refrigerator. When ready to serve, reheat the filling, stuff the squash, add cheese, and bake until bubbly. Drizzle with fresh hot honey just before serving.
- → What other squash varieties work well for stuffing?
While acorn squash is ideal for its size and sweet flavor, you can use kabocha, delicata, or butternut squash. Adjust roasting times accordingly—smaller squash like delicata may need less time, while larger varieties might require additional minutes in the oven.
- → How can I adjust the spice level?
Control the heat through three elements: include or omit the jalapeño in the filling, adjust the chili powder amount, and customize the hot honey drizzle. Start with 1 teaspoon hot sauce in the honey mixture and add more to taste. Serve with extra hot sauce on the side for heat-lovers.
- → Is this dish freezer-friendly?
The components can be frozen separately for up to 3 months. Freeze roasted squash halves in freezer bags, and store the chili mac in airtight containers. Thaw overnight in the refrigerator before reheating, stuffing, and finishing with cheese. Note that texture may be slightly softer after freezing.
- → What sides pair well with this stuffed squash?
A crisp green salad with citrus vinaigrette cuts through the richness, while cornbread complements the Southwestern flavors. Roasted Brussels sprouts or sautéed kale with garlic also work beautifully. For a lighter meal, serve half a squash per portion with a simple side.