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It’s fall, so there needs to be a lot of chili involved. Don’t cha think?

Crockpot Chipotle Pulled Pork Pumpkin Chili w/Cinnamon Roasted Pumpkin Seeds | @hbharvest

Chili is one of my favorite things about fall. It’s just so dang comforting. A big pot of chili simmering all day on the stove is the best. Especially, if it’s a cold day. Nothing beats a hot bowl of chili on a cold day.

I mean, your house smells A-maaa-zing.

Crockpot Chipotle Pulled Pork Pumpkin Chili w/Cinnamon Roasted Pumpkin Seeds | @hbharvest

Every year at about this time, I make chili. I do it without thinking, it’s just a natural habit this time of year. Actually, we pretty much always have this chili on Halloween. It’s somehow become our own little Halloween tradition. Chili on Halloween.

I realize today is the day BEFORE Halloween, but it didn’t seem to make sense to show you guys a recipe I want you to make on the very same day. And yes, I really, really, really want you guys to make this for dinner tomorrow night. And if not tomorrow, because you have party plans and such, than Sunday for sure, because this is very much a Sunday recipe too!

Crockpot Chipotle Pulled Pork Pumpkin Chili w/Cinnamon Roasted Pumpkin Seeds | @hbharvest


I know that chili is already an easy dish, but this Crockpot Chipotle Pulled Pork Pumpkin Chili is even easier. Literally you throw everything into the crockpot in the morning and then just let it cook, low and slow ALL DAY LONG. If you can, cook it the day before you plan to eat it. Then place it in the fridge overnight, get it back out the next morning and cook it again till dinner time. Honestly, the longer this chili sits, the better.

Like with most chili recipes, I always say three-day old chili is better than day old chili. Aging does this soup some good. Trust me on this.

Crockpot Chipotle Pulled Pork Pumpkin Chili w/Cinnamon Roasted Pumpkin Seeds | @hbharvest

Chili always brings back good memories for me. It’s really one of the only meals I remember my mom ever making, and she only made it on cold dreary days. Which was clearly perfect. Chili on a sunny, semi-warm day is just not what I want. Cold days put me in the mood for chili. You know?

AND mom always served her chili Cincinnati style. Not gonna lie you guys, I sort of think all chili should be served this way, and with a hefty side of beer bread too, because well, it just should.

When I serve this for dinner, I serve it over angel hair pasta. I really just do not know any other way to serve chili. It’s pasta, topped with saucy delicious chili and cheddar cheese. So flipping good. Do what you please, but I highly recommend serving this Cinci Style.

Crockpot Chipotle Pulled Pork Pumpkin Chili w/Cinnamon Roasted Pumpkin Seeds | @hbharvest

Also, if you like your chili full of texture, I would recommend browning the pork before adding it to the crockpot. This will add a little extra oomph to your chili.

Double also, I highly recommend using fresh cubed pumpkin in the chili. Sure, you can used the canned stuff in a pinch, but the cubes of pumpkin add some much needed texture and great flavor. I loved biting down into the sweet pumpkin. I am way too into the pumpkin right now…. as you will see tomorrow.

Crockpot Chipotle Pulled Pork Pumpkin Chili w/Cinnamon Roasted Pumpkin Seeds | @hbharvest

And about the pumpkin seeds.

Don’t get all freaked out because they are roasted in cinnamon sugar. The sweetness balances that spicy chipotle and the crunch just builds on the texture. You can’t skip the seeds you guys. One, you really do need them for the texture. They add a nice crunch and breakup the smoothness of the pork. Two, they are so delicious. It’s possible you may eat the whole pan before you serve the soup, in which case you obviously should make another batch. And you better double it while you’re at it.

Ok, so here is you game plan.

Start your chili today, let it sit overnight… heat it back up tomorrow!

Crockpot Chipotle Pulled Pork Pumpkin Chili w/Cinnamon Roasted Pumpkin Seeds | @hbharvest

Crockpot Chipotle Pulled Pork and Pumpkin Chili w/Roasted Pumpkin Seeds.

Prep Time 40 minutes
Cook Time 6 hours 30 minutes
Total Time 7 hours 10 minutes
Servings: 6
Calories Per Serving: 718 kcal

Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.


Cinnamon Sugar Pumpkin Seeds


  • Add the pork to the bowl of a crockpot. Drizzle the honey over the pork and then sprinkle with chili powder, chipotle chili powder, cinnamon, garlic powder, onion powder, cayenne and season with 1/2 teaspoon salt. Add the bay leaves and then pour in the beer, cider vinegar, worcestershire, fire roasted tomatoes and tomato paste. Add the cubed pumpkin and stir to combine.
  • Cover the crockpot and cook on low for 7-8 hours or on high for 4-6 hours (I recommend going low and slow).
  • Just before you are ready to shred the pork, make the pumpkin seeds. Preheat the oven to 350 degrees.
  • In a heavy-bottomed medium skillet, add the butter and melt over medium heat until just browned. Butter will melt, foam, and froth, and then begin to brown along the bottom. Whisk the browned bits off of the bottom of the pan. Remove from the heat and stir in the pumpkin seeds, brown sugar, cinnamon and salt. Toss well and then spread the mixture out onto a parchment lined baking sheet. Roast for 20-30 minutes, stirring every 10 minutes to make sure nothing is burning. Remove from the oven. Taste and season with salt if desired.
  • Remove the pork from the crockpot and let cool slightly. Lightly shred the pork with two forks or your hands and return the meat to the crockpot. Add the black beans. Toss well, cover and warm through. If the chili base is too thin for you liking, add a cup or so of chicken broth until your desired consistency is reached.
  • To serve, ladle the chili into bowls. Top with a dollop of greek yogurt and shredded cheddar cheese. Sprinkle the the pumpkin seeds over the chili. EAT!!
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Crockpot Chipotle Pulled Pork Pumpkin Chili w/Cinnamon Roasted Pumpkin Seeds | @hbharvest

Best Halloween dinner ever. No really. All you need is a side of candy. Oh, and it’ll be Friday, so this is clearly all a win, win!

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  1. 3 stars
    I’ve made hundreds of HBH recipes and LOVED majority of them. Have all your cookbooks in my kitchen and you are truly my go-to for inspiration and ideas! Thank you for years of spectacular meals. Unfortunately, this one just didn’t dance on the taste buds like the others have. Likely a personal preference, but I would not make this one again. Looking forward to trying another recipe very soon! Have a great day. Be well.

    1. Hi Whitney! I am so sorry this recipe wasn’t enjoyed! thank you for letting me know! Have a wonderful weekend! xT

      1. Hey there! Maybe something went wrong with the cooking. It’s seriously one of the best dishes Ive ever had. I suggest you try it again. It’s amazing.