Roasted Chestnut and Herb-Stuffed Winter Squash

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

A cozy roasted winter squash filled with savory chestnuts, fresh herbs, and aromatic vegetables, perfect for a festive holiday meal. This Mediterranean Christmas recipe (vegetarian), ready in about 60 minutes, pairs small acorn squash, olive oil, and chopped yellow onion for a weeknight-friendly dinner. Each serving lands at about 320 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 "Build a week of meals around this recipe" 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.

Ingredients

• 2 whole small acorn squash
• 3 tbsp olive oil
• 1 cup chopped yellow onion
• 3 minced garlic cloves
• 1 cup roasted chestnuts, chopped
• 2 tbsp chopped fresh sage
• 1 tbsp chopped fresh thyme
• 1/3 cup dried cranberries
• 1 cup cooked quinoa
• 1 tsp salt
• 1/2 tsp black pepper

The sheet pan we’d roast this on → Best Sheet Pans in 2026: Top Picks + Buying Guide

Instructions

1. Step 1: Preheat oven to 400°F. Cut 2 small acorn squash in half and scoop out seeds. Brush each half with 1 tbsp olive oil and season with 1/2 tsp salt and 1/4 tsp black pepper. Place cut side down on a baking sheet and roast for 30 minutes until tender and edges caramelize.
2. Step 2: While squash roasts, heat 2 tbsp olive oil in a skillet over medium heat. Add 1 cup chopped yellow onion and sauté for 5 minutes until translucent. Add 3 minced garlic cloves and cook for 1 minute until fragrant.
3. Step 3: Stir in 1 cup chopped roasted chestnuts, 2 tbsp chopped fresh sage, 1 tbsp chopped fresh thyme, and 1/3 cup dried cranberries. Cook for 2 minutes to combine flavors.
4. Step 4: Remove skillet from heat and mix in 1 cup cooked quinoa, then season with 1 tsp salt and 1/2 tsp black pepper. Spoon the mixture evenly into the roasted squash halves.
5. Step 5: Return stuffed squash to oven and bake for an additional 10 minutes at 400°F until the filling is heated through and edges are lightly browned. Serve warm.