For all the squash recipes I do, pumpkin remains underrepresented, with only uses in a soup and ravioli to date. Pumpkin's seasonality, and the fact that it's not a favorite of mine, are the drivers behind its low use, but around this time last year I was prepping for a Meatwave that was going to happen on Halloween weekend, and while out shopping I saw a giant bin of sugar pumpkins. In that moment, I felt like I needed to swap the intended butternut squash for them because it just fit the theme too well, plus it created a reason for me to give pumpkins a shot at something I would really enjoy when I made them into these pumpkin quesadillas.
When choosing to cook with pumpkins, its the small sugar variety that you're after. They may look like mini versions of the common jack-o-lantern variety, but they're actually sweeter and less fibrous, making them ideal for consumption, while their larger brethren are best left for carving.
Their use in quesadillas had me devising a seasoning for the pumpkins beyond the standard salt and pepper. I opted to sprinkle my halved and seeded orbs with a mixture of dark brown sugar, cumin, and chili powder to introduce an earthy spice into the flavor profile, along with a boost in sweetness.
I wanted a little extra sugar because I was going to be adding slightly spicy Anaheim peppers into the quesadilla filling mixture. While these peppers aren't overly hot, they can have a good kick to them to go with their pronounced fruity flavor. To prepare them, I first charred them completely over a batch of freshly lit coals, then set them in a covered container to steam and cool for about ten minutes, and finally removed the skins, stems, seeds, and finely chopped the remaining flesh.
During that time, I had the pumpkin halves roasting over indirect heat. It had been so long since I've grilled pumpkin, I wasn't quite sure how long they would take to fully tenderize, and when that clocked in at around 45 minutes, I wondered if maybe I should have chunked up the pumpkins for quicker cooking. Since I'm not sure how long it would take to cook smaller pieces, and the fact that this method worked well, I kept the halved preparation and long roasting time in the final recipe, but feel free to try some adjustments if you want to see if you can speed things up.
Once the pumpkins were tender and cooled a bit, the flesh was easy to scoop out and divorce from the skin with a spoon. I dumped all those innards into a large bowl and began building the filling by mashing them together sour cream, cilantro, scallions, and the chopped peppers. I was a little put off by the stringy texture on my first taste, so I kept mashing a bit more to break down the flesh into a finer, and creamier mixture that vibed with my palate.
One of my goals with these quesadillas was to be able to grill them quickly while my guests were all there, so I actually assembled them all in advance before anyone even arrived. I did this by buttering one side all the tortillas, and then spreading a layer of the pumpkin mixture on an unbuttered half, followed by a layer of pepper jack cheese, and finally topping with another tortilla.
Then all I had to do while I was entertaining was to grill each quesadilla long enough to melt the cheese and brown the tortilla. It's best to do this over direct heat with the fire running at a medium temperature. The fire was still too hot for my first few quesadillas and they browned and started to blacken before the cheese could melt, but I made adjustments as I went along, so most of the quesadillas that came off the grill were golden brown, crisp, and had cheese that oozed out a bit when sliced.
In the end, I wasn't left a pumpkin convert—I still would have preferred butternut squash—but my guests didn't have the same qualms as me and gobbled these up. I did dig the flavor overall with a mellow sweetness that allowed the earthiness of the spices to come through, along with the heat of the peppers too. The filling had a nice tang to it from the sour cream, and the overall creaminess helped the pumpkin mixture meld with the cheese in way that it tasted totally cohesive in the final quesadilla. I enjoyed giving grilling pumpkins another shot, and think this is my best and more creative recipe with them, but alas, they'll probably remain a mere novelty on this site as I'm most likely continue to rely on my other preferred orange squashes at this time of year.
- Yield 4 servings
- Prep 15 Minutes
- Cook 1 Hour
- Total 1 Hour 15 Minutes
- 2 teaspoons dark brown sugar
- 1 1/2 teaspoons chili powder
- 1 1/2 teaspoon kosher salt, plus more to taste
- 1/4 teaspoon ground cumin
- 1 tablespoon canola oil
- 2 sugar pumpkins, steemed, halved, and seeded
- 4 Anaheim peppers
- 1/4 cup sour cream
- 3 tablespoon finely minced fresh cilantro
- 3 tablespoons finely minced scallions
- 8 8-inch flour tortillas
- 2 tablespoons butter, at room temperature
- 8 oz grated pepper jack cheese
- In a small bowl, mix together brown sugar, chili powder, salt, and cumin. Brush the inside of each pumpkin half with oil and season with spice mixture.
- Light one chimney full of charcoal. When all the charcoal is lit and covered with gray ash, pour out and arrange the coals on one side of the charcoal grate. Set cooking grate in place, cover grill, and allow to preheat for 5 minutes. Clean and oil grilling grate. Place peppers on hot side of grill and cook, turning occasionally, until completely charred all over, about 10 minutes total. Transfer peppers to a medium bowl, cover with plastic wrap, and set aside.
- Place pumpkin halves on cool side of grill, cover, and cook until pumpkin flesh is completely softened and has begun to brown in spots, about 45 minutes. Remove pumpkins from grill and let rest until cool enough to handle.
- Peel skins off of pumpkin halves and transfer flesh to a large bowl. Add sour cream, cilantro, and scallions into bowl with pumpkin flesh. Using a potato masher or whisk, mash mixture until pumpkin is very smooth and all ingredients are well combined. Season with salt and pepper to taste.
- Remove charred skins, deseed, and roughly chop peppers. Butter one side of each tortilla. Spread a layer of the pumpkin mixture on the unbuttered side of 4 tortillas. Top pumpkin mixture with pieces of chopped peppers to taste, followed by a layer of cheese. Place remaining tortillas on top, buttered side up.
- Replenish grill with 2/3 a chimney of freshly lit coals arranged evenly across the charcoal grate. Place quesadillas on grill and cook, flipping occasionally, until tortillas are well browned and cheese has melted, about 5 minutes total. Transfer quesadillas to a serving platter or plates, cut each into 6 equal pieces, and serve immediately.