Roasted Squash and Sweet Pepper Chili

Roasted Squash and Sweet Pepper Chili

Whew – what a week. I know I’m probably starting to sound like a broken record – but maaaaaaaaaaan it’s been a busy week. I’m not even sure where to begin. Let’s see – I spent most of the last week trying to finish recovering from the flu. I wasn’t oh-my-god-kill-me-now-I’m-so-sick… you know the kind, where you really have no choice but to crawl in to bed because you can’t possibly function? No – I was the functionally walking ill, just well enough to feel like I should be getting things done, and just sick enough to be miserable while doing it. All week. I’m still dealing with sniffles and cough, but fortunately, the worst of the miserables are over, and I’m starting to get my energy back.

One interesting side note to my being sick – you know those headaches and icky feelings you get when you give up caffeine? Well – since I was sick anyways, and not feeling up to coffee, somehow in the last couple of weeks I managed to break my caffeine dependency. I mean, if you’re already feeling miserable, whats a little more headache, right? It wasn’t planned – but since it happened, I’ve been kind of enjoying it. I’ve had a little bit of coffee recently, but we’re talking about maybe a shot or two of espresso once or twice a week… instead of four shots of espresso every day. I doubt it will last very long. Mr. Man has absolutely no intention of giving up his coffee, and as long as it’s around, with it’s temptingly caffeiney aroma, it will be much harder to give up completely, let alone prevent a complete relapse.

Goats Eye Beans

In addition to my recovery from the flu – Miss Thing had extra practices last week, a game plus extra practice on Saturday, and then we went to Marine World on Sunday. So yeah. Busy-busy-busy. Marine World was fun – but draining. Mr. Man convinced me to go on one of those spinning rides, and I ended up getting a little ill towards the end of the day – but we had a lot of fun hitting the roller coasters and what have you before that. Marine World might have been a little more fun if it’d been warmer. The weather has turned cooler. It’s been downright nippy the last week or so. Which has had me breaking out the soup pot more often lately – something that Miss Thing is no doubt unahppy about, but that I’ve been really enjoying. I’ve had a hard time turning over some of my pantry staples the last year or so – so when I decided to make this chili, I went hunting around and found these Eye of the Goat Heirloom beans that I’ve had for some time. They ended up being really spectacular in the chili – and I can now say that I’m an heirloom-bean-convert. These were much better than any other canned or dried bean I’d had before. Full of flavor and texture. In fact – I went poking around on some heirloom bean websites, thinking about ordering some, and had to stop myself from buying one of everything. I think I’ll wait until the first blush of infatuation has passed and then decide what I really want to try.

Cooked Goat Beans

If you don’t have have Eye of the Goat beans – you can use any type of Pinto style bean. (I suppose you could skip the bean-cooking-process and use canned, too – if you really wanted to…), the flavor will be a little different, but should still be really good. You might be surprised to find out though, that this chili has absolutely no tomatoes in it. Cross my heart – it’s that red from the squash and sweet peppers. So all you Tomater-Haters, enjoy! However, if you were to use orange or yellow sweet peppers, your color may vary – but it will still taste good. When you make up this chili, you can do several of the steps in different parts, over the course of a couple of days even – if you’re short on time. I had the day kind of planned out for making this dish, so I was able to get it done in one day – but I’ll admit, it was time consuming and at one point I had to leave for several hours and then come back to finish it.

Roasted Peppers

I roasted the peppers and squash in the morning, had the beans cooking on a back burner, and made Scrap Stock for some of the stock in the chili. (Now that it’s getting cooler again I figured I should probably stop being lazy and start making stock again…) In the afternoon I came home and assembled everything and simmered for a couple of hours to finish cooking. The plan was to serve it with some Anadama Bread that Mr. Man was baking – but unfortunately, the bread wasn’t ready until long after everyone was hungry and wanting to eat, so we served it with crackers – which was almost as good. ;-) My roasted peppers got a little more… roasted… than I intended them to, but it didn’t end up being a problem. For those of you trying this at home though – I’d suggest stopping the roasting process a little bit sooner. Oh – I almost forgot. I didn’t roast the Cayenne Peppers I threw in there, because I didn’t find them at the store until after the rest of the peppers had been roasted, but it really didn’t matter that much. And if you can’t find fresh Cayenne Peppers (They aren’t particularly common after all) just use as much powdered cayenne pepper as you like instead.

Unsweet Cocoa

When I was younger (before I learned to cook) I used to buy those seasoning packets for things like chili, gravy, soups, etc… and add them to the dishes I was preparing. At the time it was definitely a step up from the boxed mac-and-cheese and hamburger helper that I had relied upon before that. Eventually it happened that I had assembled everything for chili and realized that I didn’t have one of those seasoning packets for chili. I tried everything I could think of to make it taste right, probably dumped in far more seasoning from my spice rack than was neccessary, and was about to pull my hair out in frustration when it occurred to me to look on the interwebs (hey – I was young… and so was the internet! It was a long time ago… don’t mock me.) And I discovered that the secret ingredient to good chili was Unsweetened Cocoa. It was kind of a revelation for me – and probably marks the beginning of my move away from spice packets and getting to where I began to cook more things from scratch. However, I can say that at the very least, from that point on, I never bought another Chili Spice Packet again.

At any rate, I was inspired to make this chili when I received an Acorn Squash in this week’s FFTY box. I wanted to make something a little different, try something new. The sweet peppers I’d managed to develop a back log on, so it seemed like a great way to use them up too. I’ll admit – the acorn squash flavor wasn’t quite as strong as I was hoping, so I might have to experiment with this recipe a little more and see what I can do about that, but it was still delicious. In fact – Mr. Man said it was the best Chili he’d ever had, ever. Oh – one last thing… I had intended this chili to be served alongside bread of some kind. Corn Bread, Anadama bread, etc… So I didn’t use any thickener really – it was still nice and hearty anyways, but if you prefer your chili a little thicker, I’d recommend making adding a couple of tablespoons of flour to the browned sausage and onions to make a roux.

Detail Roasted Squash and Sweet Pepper Chili


  • 1 Acorn Squash; washed
  • 2 lbs Sweet Peppers; seeded and halved (quartered for large peppers)
  • 1 lb Mild Italian Sausage
  • 12 oz Eye of the Goat Beans (or other dried pinto-style beans – or substitute with canned beans)
  • 3 quarts Stock (I used 2 quarts Scrap Stock and 1 quart Chicken Stock – if using Canned Beans, you’ll only need 2 quarts)
  • 1 Onion; diced
  • 4 cloves Garlic; minced
  • 3 Jalapeno Peppers
  • 2 Serrano Peppers
  • 4 Fresh Cayenne Peppers
  • 2 tbs Unsweetened Cocoa
  • 2 tbs Cider Vinegar
  • 2 tsp Cumin
  • Olive Oil
  • Kosher Salt to taste


  • The night before you want to make chili:
  • Rinse and pick over the Dried Beans
  • Soak the Beans overnight
  • Drain the beans, and place in to a heavy pot with a tight fitting lid (recommend dutch oven)
  • Add 1 quart of the stock, and enough water to cover the beans by 2 inches (if neccessary, during the cooking process, add more water to keep the beans covered by atleast 2 inches of liquid)
  • Bring to a boil, then reduce heat, cover, and simmer – stirring occasionally until beginning to become tender.
  • Add a couple pinches of kosher salt to the beans and continue simmering and stirring occasionally until beans are cooked to desired tenderness
  • While the beans are cooking – prepare the squash and peppers.
  • Preheat Oven to 350° and place the whole acorn squash in a baking pan
  • Place in the oven and roast until cooked through. Set aside to cool.
  • For the peppers, place the seeded and cut sweet peppers in to a roasting pan, along with the (whole) jalapeno peppers and serrano peppers
  • Toss with olive oil and sprinkle liberally with kosher salt
  • Roast for 30 minutes, or until tender and beginning to turn golden brown along edges. Set aside to cool.
  • Peel and seed the cooled squash (peel should just pull right off)
  • Puree the squash in a blender until smooth (add some of the stock if neccessary)
  • Transfer the squash to a bowl and set aside until ready to assemble the chili
  • Place the sweet peppers in to the blender and puree until smooth (add stock if neccessary)
  • Transfer most of the sweet peppers to the squash, reserving about 1/2 a cup of Sweet Pepper Puree in the bottom of the blender, and set aside until ready to assemble the chili
  • Add the Serrano Peppers, Jalapeno Peppers, and Cayenne Peppers to the reserved Sweet Peppers in the blender. Puree until smooth (add stock in neccessary)
  • Transfer to a small bowl and set aside
  • In a large, heavy pot – begin browning and crumbling the sausage. When cooked, add the onions and saute until translucent.
  • Add the garlic, and squash-sweet pepper mixture, stirring to combine
  • Begin adding remaining stock, stirring to combine
  • Add the cooked beans, cider vinegar and kosher salt
  • Take the cocoa powder and place it in to a small bowl.
  • Stir in the cumin and a couple spoonfuls of the Spicy-Pepper Puree until smooth (can use the stock from chili instead for milder)
  • Add the cocoa-pepper mixture to the chili and test for heat
  • Add additional spicy pepper mixture to the chili until desired heat level is reached  (to taste)

3 Responses to “Roasted Squash and Sweet Pepper Chili”

  1. I can’t wait to try this recipe out. I am on a really big chili kick since fall hit!


  2. [...] Roasted Squash and Sweet Pepper Chili at [...]

  3. This souns interesting and delicious! I love all those flavors!

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