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Heat oven to 375F. Place diced pumpkin on a rimmed baking sheet, toss with 1 TB olive oil and about 1 tsp (+/-) spice mixture. Toss to coat evenly. Roast for 12-15 minutes until just tender. Set aside. Option to toast the pumpkin seeds after pumpkin is done ~ 350F, 10 min.
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While the pumpkin is roasting, heat 1 TB olive oil in large pot over medium-high heat. Add chopped onions and a couple pinches of salt. Cook until soft and beginning to brown, stirring often, about 8 minutes.
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Add garlic and 2 tsp of the spice mixture. Stir until fragrant, about 1-2 minutes. Add tomatoes with juice, beans, and oregano.
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Add 2 cups broth. Bring to boil and add the bulgur wheat. Cover and reduce heat to medium-low. Simmer about 30 minutes until bulgur is tender.
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Stir squash into chili, season with salt and pepper. Divide chili among bowls.
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Add desired toppings!