Making a quesadilla for dinner is a lot like walking out of your pants the moment you step through the door – it’s bliss, a relief, a reward. Or at least that’s how I look at it. Quesadillas are a simple pleasure. They can be delicious with nothing more than cheese, or life-changing when more elaborate. And therein lies what I love most about the quesadilla, their versatility. You can stuff any sad thing for your crisper into them and transform it from yuck to yum. But today we’re not making quesadillas out of necessity, we’re making them on purpose. These Acorn Squash Quesadillas are far from flung together but they still feel carefree, fun, and most importantly, cozy.
It’s darker than dark in my neck of the woods. The nights are starting earlier and the mornings are pitch black. I really struggle with the lack of daylight. It affects my mood swiftly and brutally. But there is one thing I love about the lack of light and that’s comfort food. In the summer it makes no sense to hunker down with a gooey, cheesy anything. And if you do submit to your need for couch and pasta time in the middle of July, you’re likely plagued with guilt for not taking advantage of the gorgeous, short-lived weather. But in November? Who’s going to feel bad about standing up cold drizzle?
Yes, this is prime time for comfort food. It’s really the only thing late fall and winter has going for it. Even I can admit coming in from the cold to a warm bowl of soup is undeniably glorious. I mean, I might not feel that way once February sets in, but for now, I’m on team cozy. So let’s make everything with all the cheese like these Acorn Squash Quesadillas.
This recipe kicks off by splitting an acorn squash. Personally, I love squash recipes that only require one cut. They are a tough nut to crack after all and any day I don’t have to peel a squash is a good one. Once the squash is split. Deseed it and fill the cavity with a pat of butter and a little honey. You don’t have to add the honey but I quite like the hit of sweetness. Finish dressing the squash with a drizzle of olive oil and a generous sprinkle of salt. Add chili flakes if you’re looking for a bit of spice. Pop the squash into the oven and roast it for an hour or more. We want the squash to be very very tender.
While the squash is roasting, shred some green cabbage. I only used a third of a head of cabbage for this because you will find when you shred a cabbage, the results are rather voluminous. But if you’re looking to make a lot of quesadillas, feel free to shred more. To the cabbage add half a red onion sliced thin, and a jalapeño shaved on a mandoline. Then, we’re going to add a cocktail of lime juice, olive oil, a clove’s worth of minced garlic, and some salt. Give it a toss and set it aside to marinate. The cabbage will soften and the raw onion flavor will mellow. Honestly, the mixture will just improve with time, so tackle this the moment your squash enters the oven.
Once the squash is effectively butter, scoop the flesh out of the skin and place it in a large bowl. Make sure to get as much of the melted butter and honey into the bowl as possible. To the squash add another clove of minced garlic and 2 heaping tablespoons of sour cream for tang and a little extra creaminess. Mix everything together until cohesive. You likely won’t need more than a fork or two to achieve this. If the squash has been roasted for an ideal amount of time, it should positively fall apart with the slightest encouragement.
With the squash and cabbage ready, it’s time to build the quesadillas. Start by spreading some of the squash mixture on one flour tortilla. Top the squash with shredded cheese. I used Oaxaca cheese but if you can’t get it where you are, you can sub it for low-moisture mozzarella. I selected Oaxaca cheese for its subtle flavor and melting prowess both of which mozzarella has in spades. In other words, we want a cheese capable of a solid cheese pull. Top the cheese with the cabbage mixture and yet more cheese. Spread the squash over another tortilla and place it on top, squash-side-down.
Transfer the assembled quesadilla to a generously oiled frying pan and fry until golden on both sides. Keep your finished quesadillas warm in a low 150°F oven and repeat until all the quesadillas are finished. Slice them into quarters and finish with a sprinkling of fresh cilantro, a side of sour cream and hot sauce, and an ice-cold beer, if desired. For extra cozy vibes, serve this quesadilla with a piping-hot bowl of Tortilla soup. It’s kind of like tomato soup and grilled cheese with flair.
And that’s everything you need to know about these Acorn Squash Quesadillas. So simple to prepare and satisfying to eat. For best results pair these with pajama pants and questionable television choices.
Acorn Squash Quesadillas
- 1 large frying pan
- 1 acorn squash split in half, deseeded
- 2 tbsp unsalted butter
- 2 tbsp honey
- 4 tbsp olive oil divided
- 1 tsp chili flakes I used gochugaru
- ⅓ head green cabbage sliced thin
- ½ red onion sliced thin
- 1 jalapeño sliced thin
- 2 cloves garlic minced, divided
- 1 lime juiced
- 1 tsp salt
- 1 tsp whole cumin seeds
- ¼ cup sour cream
- 12 flour tortillas
- 275g (10oz) Oaxaca cheese ** shredded
- ½ cup toasted pumpkin seeds
- ¼ cup neutral oil for frying
- fresh cilantro for serving
- Preheat the oven to 350°F.
- Arrange the squash halves on a small baking sheet lined with parchment paper. Divide the butter between the two squash cavities. Repeat with the honey. Drizzle the squash evenly with half of the olive oil and sprinkle with a generous amount of salt followed by the chili flakes. Place the squash in the oven and roast for 1 hour and 20 minutes or until very tender.1 acorn squash, 2 tbsp unsalted butter, 2 tbsp honey, 4 tbsp olive oil, 1 tsp chili flakes
- While the squash is roasting, place the cabbage, red onion, and jalapeño in a large bowl and set it aside. In a small bowl whisk to combine half of the garlic, lime juice, salt, and the remaining olive oil. Pour the mixture over the cabbage and toss to coat. Transfer to the fridge and chill until ready to use.⅓ head green cabbage, ½ red onion, 1 jalapeño, 2 cloves garlic, 1 lime, 1 tsp salt
- Pour the cumin seeds into a large dry skillet and toast them over medium heat. Transfer them to a bowl and set them aside.1 tsp whole cumin seeds
- When the squash is done, scoop the flesh out of the skin and place it in a large bowl. Add the remaining garlic, the cumin seeds, and the sour cream. Smash and mix the ingredients together until well-combined.¼ cup sour cream
- Spread some of the squash mixture on one of the tortillas. Top the squash with a healthy sprinkling of the cheese and some of the cabbage mixture. Top the cabbage with another round of cheese and a sprinkling of pumpkin seeds. Spread some of the squash on a second tortilla and place it on top, squash-side-down. Repeat with the remaining tortillas.12 flour tortillas, 275g (10oz) Oaxaca cheese **, ½ cup toasted pumpkin seeds
- Heat the neutral oil in the skillet you used to toast the cumin seeds. When the oil is shimmering, place the quesadilla in the pan. Fry over medium-low heat until golden on both sides. *** Store the finished quesadillas in a low 150°F oven and repeat with the remaining quesadillas.¼ cup neutral oil
- Slice the quesadillas into quarters and top them with fresh cilantro and serve them alongside hot sauce and additional sour cream.fresh cilantro