Save to Pinterest This festive main dish is a true showstopper for any autumn gathering. Tender acorn squash halves are filled with a savory orzo and pumpkin mixture, crowned with a tangy cherry glaze that delivers just the right touch of sweetness. With its jewel tones and richly layered flavors, this recipe always takes center stage at my family’s holiday tables.
The first time I baked these for a potluck my friends kept sneaking extra spoonfuls of the pumpkin orzo filling straight from the pan. It has become our favorite excuse to invite people over when the air turns crisp.
Ingredients
- Acorn squash: firm and deeply colored for best roasting and beautiful presentation
- Olive oil: brings out the natural sweetness of the squash and helps everything caramelize
- Salt and black pepper: enhances all the autumn flavors use freshly ground
- Orzo pasta: makes the stuffing hearty and toothsome choose bronze cut orzo if possible
- Yellow onion: mild and sweet when cooked providing savory backbone
- Garlic: always brightens the base choose plump cloves for freshness
- Pumpkin purée: delivers rich creamy texture and autumn flavor pick pure pumpkin not pie filling
- Vegetable broth: helps blend and moisten the filling low sodium is ideal
- Parmesan cheese: melts into the mix for savory richness and a little tang opt for real Parmigiano Reggiano
- Walnuts: add crunch and toasty flavor try to source freshly shelled nuts
- Dried cranberries: lend jewel tone pops and sweet tart complexity read labels for unsweetened types
- Ground cinnamon and nutmeg: classic warming spices tie the filling together use freshly grated nutmeg if you can
- Fresh parsley: brings color and a final herbal note choose flat leaf for best flavor
- Cherry preserves: the base of the sweet glaze seek out preserves that contain whole cherries
- Balsamic vinegar: balances the glaze with bright acidity use a good aged vinegar if possible
- Honey: rounds out the glaze for smoother sweetness local honey has the most floral complexity
- Red pepper flakes: add a subtle kick and warmth go for crushed flakes with bright red color
Instructions
- Preheat the Oven:
- Set your oven to 400 degrees Fahrenheit and line a baking sheet with parchment paper for easy cleanup
- Roast the Squash:
- Brush the cut sides of your acorn squash with olive oil and sprinkle them generously with salt and black pepper. Place them cut side down on the baking sheet and roast for about thirty to thirty five minutes until the flesh feels tender when poked with a fork and the edges are caramelized
- Cook the Orzo:
- Prepare orzo pasta according to the package instructions in boiling salted water for maximum flavor. Drain well and set aside to cool slightly
- Sauté the Aromatics:
- Heat olive oil in a large skillet over medium heat. Add the diced yellow onion and cook until translucent about three minutes stirring so it softens without browning. Toss in the garlic and stir for about one minute releasing its aroma into the oil
- Make the Filling:
- Stir pumpkin purée and vegetable broth into the skillet with the onion and garlic. Add the cinnamon and nutmeg followed by the cooked orzo pasta. Cook for three to four minutes on medium low stirring now and then so the mixture thickens but does not stick
- Finish the Mix:
- Take the skillet off the heat. Fold in grated Parmesan toasted walnuts dried cranberries and chopped fresh parsley. Season to taste with salt and pepper stirring well so everything is evenly distributed
- Prepare the Cherry Glaze:
- In a small saucepan combine cherry preserves balsamic vinegar honey and red pepper flakes if using. Bring to a simmer over medium heat stirring until the mixture thickens and smells aromatic this should take three to four minutes. Remove from the heat and set aside
- Stuff the Squash:
- Carefully flip roasted squash halves cut side up on the baking sheet. Spoon and mound the warm pumpkin orzo filling into each hollow so it is piled slightly above the rim
- Glaze and Bake:
- Generously drizzle each stuffed squash half with cherry glaze letting it pool in spots for a beautiful glossy finish. Return the squash to the oven and bake for ten minutes until heated through and the glaze is bubbling gently
- Garnish and Serve:
- Transfer to a serving platter and sprinkle with additional fresh parsley. Serve warm with extra cherry glaze on the side if you like
Save to Pinterest I adore the cherry glaze in this recipe it reminds me of picking tart cherries in late summer with my sister and now that flavor instantly brings back laughter and sticky hands whenever I make it again
Storage Tips
Store leftovers in an airtight container in the fridge for up to three days. To reheat place stuffed squash halves covered in a low oven until warmed through. The glaze can be made in advance and kept chilled for a week
Ingredient Substitutions
Swap walnuts for pecans or hazelnuts for different nutty flavors. Replace Parmesan with a vegan cheese or a sprinkle of nutritional yeast if needed. Try using cooked quinoa or brown rice in place of the orzo for a gluten free version
Serving Suggestions
Serve this dish as the star of any fall feast accompanied by a crisp green salad. A roasted root vegetable medley makes an excellent side for this recipe. It is wonderful paired with a bright fruity Pinot Noir or a dry Riesling as the wine notes suggest
Cultural and Seasonal Inspiration
Stuffed squash goes back to old world harvest feasts where cooks would use whatever grains nuts and dried fruit they had on hand. This pumpkin orzo filling leans into both Mediterranean and North American fall flavors while the cherry glaze adds a playful modern twist. My grandmother always made the filling with barley and dried blueberries but I love how pumpkin and orzo soak up all the spices
Seasonal Adaptations
Roast delicata or kabocha squash instead of acorn for a slightly different flavor. Try adding roasted mushrooms or sautéed spinach to the filling for extra color. Substitute dried tart cherries for cranberries when available
Success Stories
A friend once told me this dish convinced her to try vegetarian meals more often and her kids ate seconds without even knowing it was healthy. One year I tripled the recipe for a family reunion and it was the first dish to vanish from the buffet table. Everyone asks for the cherry glaze recipe and I now keep a little jar on hand for cheese boards and sandwiches
Freezer Meal Conversion
These stuffed squash halves freeze surprisingly well. Cool completely then wrap each half tightly in foil and store in a freezer safe bag for up to one month. To reheat bake straight from frozen at three hundred fifty degrees Fahrenheit until hot and bubbling usually about thirty five to forty minutes covered loosely with foil
Save to Pinterest The vivid colors and irresistible scent of the glazed squash always make this a conversation piece at the table. Try it for your next gathering and wow your guests with both taste and presentation.
Common Recipe Questions
- → Can I substitute another squash for acorn squash?
Yes, delicata or small butternut squash work well with similar roasting times. Adjust as needed for size.
- → What pairs well with the cherry glaze?
The sweet-tart cherry glaze complements roasted squash and nuts. Try it with roasted carrots or mushrooms as well.
- → Is it possible to make this vegan?
Absolutely! Use vegan Parmesan or skip the cheese. All other ingredients are plant-based.
- → Can the stuffed squash be made ahead?
Yes, assemble and refrigerate before final baking. Reheat and add cherry glaze just before serving.
- → What can I use instead of walnuts?
Pecans or hazelnuts provide a similar crunch and nutty flavor—swap in equal amounts as desired.
- → Is this suitable for gluten-free diets?
Swap orzo for gluten-free pasta or cooked rice to adapt the filling for gluten-free needs.