Stuffing-Stuffed Acorn Squash with Cranberry Glaze

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

Roasted acorn squash halves filled with savory herb stuffing and topped with a tangy cranberry glaze for a festive vegetarian main or side. This American-inspired Thanksgiving recipe (vegetarian), ready in about 70 minutes, pairs acorn squash, olive oil, onion for a weeknight-friendly dinner that comes together with one pan and minimal cleanup. 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 "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.

Ingredients

• 2 medium, halved and seeded acorn squash
• 3 tbsp olive oil
• 1 medium, finely diced onion
• 2, finely diced celery stalks
• 3, minced garlic cloves
• 4 cups whole wheat bread cubes
• 1/4 cup, chopped fresh parsley
• 1 tbsp, chopped fresh sage
• 1 cup, warm vegetable broth
• 1/3 cup dried cranberries
• 1/2 cup fresh cranberries
• 2 tbsp pure maple syrup
• 1 tbsp balsamic vinegar
• 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. Brush 2 medium acorn squash halves with 1 1/2 tbsp olive oil each and season with 1/2 tsp salt and 1/4 tsp black pepper. Place cut side down on a baking sheet and roast for 35 minutes until tender.
2. Step 2: While squash roasts, heat 1 1/2 tbsp olive oil in a skillet over medium heat and sauté 1 medium finely diced onion, 2 finely diced celery stalks, and 3 minced garlic cloves for 5-7 minutes until softened and fragrant.
3. Step 3: In a large bowl, combine 4 cups whole wheat bread cubes, the sautéed vegetables, 1/4 cup chopped fresh parsley, 1 tbsp chopped fresh sage, and 1/3 cup dried cranberries. Pour in 1 cup warm vegetable broth and mix gently until bread is moistened but not soggy.
4. Step 4: Remove squash from oven and turn cut side up. Stuff each half generously with the prepared stuffing mixture.
5. Step 5: In a small saucepan over medium heat, combine 1/2 cup fresh cranberries, 2 tbsp pure maple syrup, and 1 tbsp balsamic vinegar. Cook for 8-10 minutes until the cranberries burst and the glaze thickens.
6. Step 6: Spoon the warm cranberry glaze over each stuffed squash half and return to oven for 10 minutes to meld flavors before serving.