Prepare the chicken. Begin by salting the chicken thighs with kosher salt. Massage the salt into the chicken and place the chicken thighs into a bowl.
Add the garlic, olive oil, balsamic vinegar, pepper and thyme to a separate bowl and whisk all of the ingredients together until combined. Pour the marinade over the chicken thighs and use your hands to massage the marinade into the chicken. Cover the bowl and place the chicken into the refrigerator for 30 minutes.
Prepare the veggies. While the chicken is marinating, add the butternut squash and red potatoes to a large bowl. Drizzle the vegetables with olive oil and toss. Add the salt, pepper, thyme, and garlic powder to the vegetables and toss until the butternut squash and potatoes are coated in spices. Set aside.
Prepare the pepitas. Add the pepitas, maple syrup, chili powder, cayenne pepper, and salt to a bowl and toss until the pepitas are coated.
Heat a skillet over medium heat and add the pepitas to the skillet. Toast in the skillet for 5-7 minutes or until they begin to turn a golden brown color. Be sure to move the pepitas around every few minutes to be sure they don’t burn.
When the pepitas are browned, carefully remove them from the heat and pour them on parchment paper to cool.
Preheat the oven to 375ºF and remove the chicken from the fridge and let the thighs sit out for 10 minutes before searing. Heat a large skillet or a dutch oven with high sides (we used a cast iron skillet with 4-5 inch sides) over medium/high heat. Add 1.5 tablespoons of olive oil.
When the olive oil is fragrant, let the marinade drip from the chicken thighs and then place the chicken thighs skin-side down in the skillet and let the chicken sear for 4-5 minutes. Be sure to gently move the chicken while it is searing to be sure the skin isn’t sticking to the pan. Flip the chicken thighs and let them cook for an additional 5 minutes on the other side. Remove the chicken from the skillet and set aside.
Leave the chicken drippings in the skillet and add the onions to the skillet. Cook the onions for 2-3 minutes and sprinkle with a pinch of salt. Add the garlic and cook for an additional 1 minute.
Add the wine to the pan to deglaze the pan and then add the butternut squash and potatoes to the skillet and toss with the onions and garlic. Cook the butternut squash and potatoes for 4-5 minutes.
Add the uncooked orzo to the skillet and toss with all the other ingredients. Let the orzo toast in the pan for 2-3 minutes.
Finally, add the chicken broth, kale, thyme, rosemary, salt and pepper to the skillet and stir together. Drizzle the heavy cream over all of the ingredients and mix again.
Place the chicken thighs on top of all of the other ingredients and cover the skillet.
Place the skillet in the oven and bake at 375ºF for 15 minutes. Uncover the skillet and let it bake for an additional 10 minutes.
Remove the skillet from the oven and let it rest for 5-10 minutes to allow any liquid to absorb. Be sure the internal temperature of the chicken is 165ºF.
Sprinkle the pepitas, cranberries, and goat cheese over the top of the skillet and enjoy!