Caramelized Onion and Bacon-Stuffed Acorn Squash

By AislePrompt Editorial · Published 2026-04-26 · Updated 2026-04-26

How this recipe was made — this recipe was drafted by AislePrompt's AI-assisted pipeline from technique templates and USDA-sourced nutrition data, and published by AislePrompt Editorial — see how AislePrompt recipes are drafted and published.

Roasted acorn squash halves filled with a savory mix of caramelized onions, crispy bacon, and herbs for a festive autumn side dish. This American-inspired Halloween recipe (vegetarian option), ready in about 65 minutes, pairs acorn squash, bacon strips, yellow onion for a weeknight-friendly dinner that comes together with one pan and minimal cleanup. Each serving lands at about 350 calories and feeds 4, so it slots cleanly into a weekly meal plan and pairs well with a quick salad or grain on the side. Tap "Plan a meal with the AI" below to drop this recipe into your week and send the ingredients straight to Instacart. Nutrition values are approximate, calculated from USDA FoodData Central (fdc.nal.usda.gov) — verify against ingredient labels for any health-driven dietary plan.

Prep: 15 min Cook: 50 min Serves 4 American cuisine 350 cal/serving

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Ingredients

2 medium, halved and seeded acorn squash
6 slices, chopped bacon strips
1 large, thinly sliced yellow onion
2 tbsp olive oil
1 tbsp fresh thyme leaves
1 tbsp maple syrup
1 tsp salt
1/2 tsp black pepper
1/2 cup crumbled (optional) goat cheese

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Instructions

Step 1: Preheat oven to 400°F. Rub 2 halved and seeded acorn squash with 1 tbsp olive oil and sprinkle 1/2 tsp salt on cut sides. Place cut side down on baking sheet and roast for 30 minutes until tender.
Step 2: While squash roasts, heat 2 tbsp olive oil in a skillet over medium heat. Add 6 chopped bacon slices and cook for 5 minutes until crispy and fat rendered.
Step 3: Add 1 large thinly sliced yellow onion to bacon; cook 15 minutes stirring occasionally until onions are deeply caramelized and golden brown.
Step 4: Stir in 1 tbsp maple syrup, 1 tbsp fresh thyme leaves, 1/2 tsp salt, and 1/2 tsp black pepper; cook another 2 minutes until syrup is absorbed.
Step 5: Remove squash from oven and turn cut side up. Fill each half evenly with caramelized onion and bacon mixture.
Step 6: Optionally, sprinkle 1/2 cup crumbled goat cheese over the filling. Return to oven and bake for an additional 10 minutes until cheese softens and edges brown slightly.
Step 7: Let cool 5 minutes before serving to allow flavors to meld.