Heat oven to 350 F. In a large mixing bowl combine piloncillo, cumin, butternut squash and whole carrots. Toss to evenly coat and place on large baking dish. Roast in oven for 30 minutes, or until golden brown.
Allow to cool slightly, reserving about a quarter of the roasted vegetables. Cube carrots into bite-size pieces. Set aside.
In a medium-sized pot (8-quart works well) heat olive oil. Saute about half the garlic, chipotle pepper, remaining carrots and butternut squash, and vegetable stock. Simmer for 10 minutes. Working in batches, transfer cooked stock and vegetables to blender and puree. Then return to stockpot to keep warm for serving.
Meanwhile, heat a medium-sized skillet. Add corn, Mexican squash, jalapeno, epazote or cilantro, remaining garlic and reserved butternut squash and carrots. Quickly sauté to lightly char (not burn) veggies. Keep watch and stir when needed for 3-5 minutes. Season to taste with salt.
To serve, divide soup among six bowls. Top off soup with charred vegetables. Garnish with toasted pepitas and a drizzle of olive oil.
Editor’s Note: If you can’t get Mexican squash, you can substitute zuchinni (the younger and sweeter the better). It’s possible that a local tienda has all the Mexican ingredients.