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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 | halfbakedharvest.com @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 | halfbakedharvest.com @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 | halfbakedharvest.com @hbharvest

SO.

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 | halfbakedharvest.com @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 | halfbakedharvest.com @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 | halfbakedharvest.com @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 | halfbakedharvest.com @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: 208 kcal

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

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Ingredients

  • 1 (2-3 pound) pork shoulder roast or butt
  • 4 tablespoon honey
  • 1/4 cup chili powder
  • 2 tablespoons smoked paprika
  • 2 teaspoons chipotle chili powder
  • 1 teaspoon cinnamon
  • 1 teaspoon garlic powder
  • 1 teaspoon onion powder
  • 1/2 teaspoon cayenne pepper
  • 2 leaves bay
  • 1 (12 ounce) beer, i used pumpkin beer
  • 2 teaspoons cider vinegar
  • 2 teaspoons worcestershire
  • 1 (28 ounce) can fired roasted crushed tomatoes
  • 2 (6 ounce) cans tomato paste
  • 4 cups fresh pumpkin diced (or 1 can pumpkin puree)*
  • 1 (14 ounce) can black beans rinsed + drained (optional)
  • shredded sharp cheddar cheese sour cream or greek yogurt and cilantro, for topping

Cinnamon Sugar Pumpkin Seeds

Instructions

  • 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 | halfbakedharvest.com @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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Comments

    1. Hi Julie! I use a 14 ounce can. Please let me know if you have any other questions. I hope you love this recipe! Thank you!! xTieghan

  1. I am thinking of cooking this a day or two in advance, putting it in the fridge overnight like you recommend, then letting it cook until lunch time the next day. when should i pull the pork?

    1. HI Nicole! You can pull the pork apart before chilling in the fridge. That will work great! Please let me know if you have any other questions. I hope you love this recipe! Thank you! xTieghan

  2. I Want to make this for my meat lovers on Halloween but I also need to make a vegetarian option chili. You think I could leave the pork out?

    1. Hi there! Sure! I would replace the pork with 3 cans of beens or lentils. Please let me know if you have any other questions. I hope you love this recipe! Thank you! xTieghan ??

  3. 5 stars
    Hi Tieghan…I just had to comment and tell you how much my family LOVES this chili! I discovered your recipe way back in 2015 (sorry it took me 4 years to comment) when we were traveling from our home in sunny Florida with constant 90 degree temps to a family reunion in the hills of Tennessee with chilly 40 degree temps. We were super excited and when my Mother-In-Law announced that we should have a family chili cook off for fun…well we did…and my Husband and I used your recipe…and guess what….we won!! Everyone was super skeptical to try it…after all who thinks of pumpkin and cinnamon for chili?! Well you…that’s who! And now we do too! We have since made it a family tradition to make it and share with neighbors every Halloween.. Thanks so much for the recipe and the family memories it has helped us make. XOXO Tracy 🙂

    1. Wow this is such a sweet story! Thank you so much for trying that recipe, Tracy! So happy it has become a family tradition!! xTieghan

  4. I already have pulled pork leftovers from smoking. Do you think it would be better to put the pork in the beginning or the end?

    1. Hey Brian! I would recommend adding the pork about 1 hour before the chili is done cooking. Please let me know if you have any other questions. I hope you love this recipe! Thank you! xTieghan

    1. HI! This will serve about 6 people. Please let me know if you have any other questions. I hope you love this recipe! Thank you! xTieghan

  5. We had this chili last night and it was an nice change from classic chili. The pork was well shredded and the pumpkin + seeds gave an extra wow. i added an extra dollop of sour cream to serve and … we ate the whole pot! By the way, I was bragging about our summer temperatures last week, now it’s almost freezing. Send in the winter food !

  6. So excited to try this recipe this week 🙂 Any sub recommendation for the beer? Not that I don’t love beer, but I’m going to let my 8 month old baby dig in on this chili (she loves chili!) Thanks!

    1. Hey Emily! YOu can use an equal amount of chicken broth (about 1 1/2 cups). Please let me know if you have any other questions. I hope you love this recipe. Thanks so much! xTieghan

  7. 5 stars
    This is what a called a real chili. Thully amazing and easy to cook, unless my father thing that all this if some kind of sauce for the seeds :DO
    Everyone like the dishes, can you also advice what i can add to make it more spice?

    1. HI! You can add in and addition jalapeno pepper or additional chipotle peppers to make this more spicer. Please let me know if you have other questions. Glad you love this recipe! Thanks! 🙂

  8. Why is it we blame kids when they whine and cajole for extra time with their devices, but then we turn around and “gift” them added tech hours when they get good grades or clean their room.

  9. Hi! Making this amazing dish again. Can I make it early and freeze it? Or make it a few days in advance? Thanks for your input!

    1. Hi! Yes! You can make it early and keep in the fridge for a few days for freeze for 2-3 months. Let me know if you have other questions. Thank you! 🙂

  10. What do you mean my 2 ounce cans of tomato paste (6). Does this mean 2, 1 ounce cans? What does the 6 mean? Thanks!!!

    1. Hi Suzanna, so sorry for the confusion. It should read 2 (6 ounce) cans of tomato paste. Recipe is now fixed. Please let me know if you have any other questions. Hope you love this recipe! Thanks! 🙂

  11. Hello,

    We love this dish! But just noticed that you listed smoked paprika under the ingredients but don’t mention in the instructions. I presume it should be added with all the other spices?