Preheat oven to 400º F. Place cubed bread on a large baking sheet. Cut off the tops of each pumpkin and set aside. Remove and discard the seeds from each pumpkin. Lightly brush 2 Tbsp. extra virgin olive oil over the insides and outsides of the pumpkin bottoms and tops and season with kosher salt and freshly ground black pepper to taste. Place on a lined baking sheet and bake for 25-30 minutes with the tops on the pumpkins, until tender. Bake the cubed bread for 7-8 minutes until toasted and set aside.
While the pumpkins are baking, prepare the stuffing. In a large Dutch oven or high-sided skillet over medium-high heat, add 2 Tbsp. extra virgin olive oil followed by the Wild Wonders peppers, apples, celery, and leek, and sage. Cook, stirring occasionally, until tender, about 5-6 minutes. Add in the toasted cubed bread and toss to combine. Add in the vegetable stock and stir to combine. Remove from heat and let stand for 5-10 minutes to allow bread to absorb the stock.
Carefully fill each pumpkin with stuffing and place back on a sheet tray. Bake for an additional 5 minutes or so, until the top of stuffing starts to crisp. Remove from oven, top each pumpkin with their tops and serve immediately.
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