When fall arrives and the air turns crisp, few dishes capture the season’s essence quite like Apple-Stuffed Acorn Squash. This recipe transforms humble acorn squash into edible bowls filled with a warm, comforting mixture of sweet apples, toasted nuts, dried cranberries, and warm spices that make your entire kitchen smell like autumn. The natural sweetness of the roasted squash pairs beautifully with the cinnamon-spiced apple filling, creating a dish that’s both elegant enough for holiday dinners and simple enough for weeknight meals. Each squash half becomes its own perfect serving, with the tender, buttery squash flesh scooped up alongside the sweet-savory filling. This dish works wonderfully as a vegetarian main course, an impressive side dish for roasted meats, or even as a light dinner paired with a simple salad. It’s the kind of recipe that makes you fall in love with seasonal cooking.
This recipe serves four people and takes about one hour from start to finish, with most of that time being hands-off roasting. Each stuffed squash half contains approximately 245 calories, giving you a nutrient-dense, satisfying meal that’s naturally gluten-free and can easily be made vegan.
1. Ingredients for the Squash
- Acorn squash – 2 medium (about 1 and 1/2 pounds each)
- Olive oil – 2 tablespoons
- Salt – 1/2 teaspoon
- Black pepper – 1/4 teaspoon
- Maple syrup – 2 tablespoons (for drizzling)
2. Ingredients for the Apple Filling
- Butter – 2 tablespoons (or coconut oil for vegan)
- Apples – 2 large (peeled, cored, and diced small)
- Yellow onion – 1 small (diced)
- Garlic cloves – 2 (minced)
- Dried cranberries – 1/3 cup
- Chopped pecans or walnuts – 1/2 cup
- Ground cinnamon – 1 teaspoon
- Ground nutmeg – 1/4 teaspoon
- Ground ginger – 1/4 teaspoon
- Brown sugar – 2 tablespoons
- Apple cider or apple juice – 1/4 cup
- Fresh thyme – 1 teaspoon (chopped, or 1/2 teaspoon dried)
- Salt – 1/4 teaspoon
- Black pepper – 1/8 teaspoon
3. Optional Toppings
- Crumbled goat cheese or feta – 1/4 cup
- Fresh parsley – 2 tablespoons (chopped)
- Extra toasted pecans – for garnish
- Additional maple syrup – for drizzling
4. Prepare the Squash
Preheat your oven to 400 degrees and line a large baking sheet with parchment paper or aluminum foil for easy cleanup. Take each acorn squash and carefully cut it in half from stem to bottom using a sharp, sturdy knife. Acorn squash can be tough to cut, so take your time and use a rocking motion with the knife rather than trying to push straight through. Once halved, use a spoon to scoop out all the seeds and stringy bits from the center cavity. You can save the seeds to roast separately if you like, just like pumpkin seeds. The cavity should be completely clean and smooth.
5. Season and Prepare for Roasting
Brush the cut sides and the cavity of each squash half with olive oil, making sure to coat them generously. The oil helps the squash caramelize and develop a rich, sweet flavor as it roasts. Sprinkle the cut surfaces with salt and black pepper. Place the squash halves cut-side down on the prepared baking sheet. This cut-side down position allows the squash to steam slightly while roasting, which speeds up the cooking process and creates tender flesh.
6. Initial Roasting
Place the baking sheet in the preheated oven and roast for 30 to 35 minutes until the squash is tender when pierced with a fork but still holds its shape. The exact time depends on the size of your squash. You want the flesh to be soft enough to eat but firm enough that the squash bowls don’t collapse. The cut sides should be golden and slightly caramelized. While the squash is roasting, you have plenty of time to prepare the apple filling.
7. Prepare the Apples
Choose firm, slightly tart apples like Granny Smith, Honeycrisp, or Braeburn that will hold their shape when cooked rather than turning to mush. Peel the apples, cut them into quarters, remove the cores, and dice them into small pieces about a quarter to half inch in size. Smaller pieces distribute more evenly in the filling and are easier to eat. You should have about two and a half to three cups of diced apples. Have all your other filling ingredients measured and ready because once you start cooking, the process moves quickly.
8. Toast the Nuts
Place the chopped pecans or walnuts in a small dry skillet over medium heat. Toast them for about three to four minutes, shaking the pan frequently, until they’re fragrant and slightly darkened. Toasting nuts intensifies their flavor dramatically and adds a wonderful crunch to the filling. Watch them carefully because nuts can go from perfectly toasted to burned in seconds. Once they’re done, transfer them to a plate to cool and stop the cooking process.
9. Cook the Apple Filling
In a large skillet, melt the butter over medium heat. Add the diced onion and cook for about three to four minutes, stirring occasionally, until it softens and becomes translucent. The onion might seem like an unusual addition to a sweet filling, but it adds a savory depth that balances the sweetness beautifully. Add the minced garlic and cook for one more minute until fragrant. Now add the diced apples to the skillet. Cook them for about five to seven minutes, stirring occasionally, until they begin to soften but still retain some texture. You don’t want them completely mushy.
10. Add the Seasonings and Liquids
Sprinkle the cinnamon, nutmeg, ginger, brown sugar, salt, and pepper over the apples. Stir everything together so the spices coat all the apple pieces evenly. The spices should smell incredible and fragrant. Pour in the apple cider or apple juice and add the fresh thyme. The liquid helps create a light glaze and prevents the filling from being dry. Let everything simmer together for about three to four minutes until the apples are tender and the liquid has mostly evaporated, leaving just enough to keep things moist.
11. Finish the Filling
Stir in the dried cranberries and the toasted nuts. The cranberries add chewy texture and tart sweetness that complements the apples perfectly, while the nuts provide crunch and richness. Cook everything together for just one more minute to heat through and let the cranberries plump up slightly from the moisture. Taste the filling and adjust the seasoning if needed. You might want more cinnamon for warmth, a pinch more salt to balance the sweetness, or a drizzle of extra maple syrup if your apples are particularly tart.
12. Flip and Fill the Squash
By now your squash should be done with its initial roasting. Remove the baking sheet from the oven and carefully flip each squash half so the cut side is facing up. The cavities are now ready to be filled. Drizzle about half a tablespoon of maple syrup inside each squash cavity, letting it pool in the center and coat the flesh. This adds extra sweetness and helps caramelize the edges. Divide the apple filling evenly among the four squash halves, spooning it generously into each cavity and mounding it slightly. The filling should fill the cavity completely and overflow just a bit.
13. Final Roasting
Return the stuffed squash to the oven and roast for another 10 to 15 minutes. This final roasting time allows the flavors to meld together, caramelizes the maple syrup, and lets the top of the filling get slightly golden and toasted. The squash should be completely tender at this point, easily pierced with a fork, and the edges might be slightly browned and caramelized.
14. Garnish and Serve
Remove the stuffed squash from the oven and let them cool for just a few minutes before serving because they’ll be extremely hot. Transfer each squash half to an individual plate. If you’re using goat cheese or feta, crumble it over the top while everything is still hot so it softens slightly. Sprinkle with fresh chopped parsley for a pop of color and freshness. You can add a few extra toasted pecans on top for crunch and visual appeal, and drizzle with a little extra maple syrup if you want more sweetness.
15. How to Eat
The beauty of this dish is that the squash half serves as an edible bowl. Use a fork to scoop up some of the apple filling along with the tender squash flesh from the sides and bottom of the cavity. The combination of the buttery, slightly sweet squash with the spiced apple filling is absolutely heavenly. Every bite should include both components for the full experience.
16. Nutritional Information Per Stuffed Squash Half
- Calories – 245
- Protein – 3 grams
- Total fat – 11 grams
- Saturated fat – 3 grams
- Carbohydrates – 39 grams
- Fiber – 6 grams
- Sugar – 20 grams
- Cholesterol – 10 milligrams
- Sodium – 320 milligrams
17. Helpful Tips
Choosing the right acorn squash is important for success with this recipe. Look for squash that are heavy for their size with hard, dull skin and no soft spots. Shiny skin indicates the squash was picked too early and won’t be as sweet. The deeper the green color with more orange patches, generally the sweeter and more mature the squash. Each squash should weigh about one and a half pounds to serve one person as a main course. If your squash are smaller, you might need three squash to serve four people. When cutting acorn squash, if you’re having trouble getting your knife through, you can microwave the whole squash for two to three minutes to soften it slightly, making it much easier and safer to cut. Always cut away from your body and use a stable cutting board. The squash can be roasted up to a day ahead. Just cool them completely, cover with plastic wrap, and refrigerate. When ready to serve, fill them and reheat in a 350-degree oven for about 15 minutes until heated through. The apple filling can also be made ahead and stored separately in the refrigerator for up to two days. For a vegan version, simply substitute the butter with coconut oil or vegan butter and skip any cheese topping or use vegan cheese. The dish is naturally vegetarian and gluten-free as written. The type of apple you choose affects the final texture and flavor. Granny Smith apples hold their shape well and provide tartness that balances the sweetness. Honeycrisp or Fuji apples are sweeter and will create a sweeter filling. A combination of tart and sweet apples often provides the best balance. Pears can be substituted for some or all of the apples for a different flavor profile. You can customize the filling in countless ways. Add cooked wild rice or quinoa for extra substance and protein, making it even more substantial as a main course. Swap the cranberries for raisins, dried cherries, or chopped dried apricots. Use different nuts like almonds, hazelnuts, or pine nuts. Add fresh sage instead of thyme for a more savory direction. For a heartier version, add cooked crumbled sausage or ground turkey to the apple mixture. The filling amount in this recipe is generous, so if you end up with extra, it’s delicious served on its own as a side dish, spooned over oatmeal or yogurt for breakfast, or used as a topping for roasted pork or chicken. If your squash won’t sit flat on the baking sheet, you can trim a very thin slice off the rounded bottom to create a stable base, being careful not to cut through to the cavity. You can also nestle them in a muffin tin to hold them steady. This dish reheats beautifully in the microwave or oven, making it excellent for meal prep. The flavors actually improve after sitting, making it a great make-ahead option for holiday meals. For an extra special presentation at Thanksgiving or dinner parties, you can add a small scoop of vanilla ice cream or a dollop of whipped cream on top just before serving for a dessert-like finish. The contrast of cold cream with warm spiced filling is incredible. These stuffed squash are naturally impressive looking and guests always think they’re much more complicated than they actually are. The individual servings make plating easy and elegant. Store any leftovers in an airtight container in the refrigerator for up to four days. They’re delicious cold, at room temperature, or reheated. This recipe celebrates the best of autumn produce and proves that seasonal, vegetable-forward cooking can be just as satisfying and crave-worthy as any meat-based dish.
