The Squashduckens: A Really Crazy Idea That (Pretty Much) Worked

As anyone who has deep-fried a turkey knows, Thanksgiving makes us do crazy things.

We had, originally, more humble goals: projects that were ambitious yet within the range of human ability.

Ali wanted to make a turducken—a nearly mythical creature so well-known that it need not be explained here. And I had my eyes on the tofurkey, a "bird" as humble as the turducken is grand, as austere as the turducken is excessive.

But turduckens are unattractive (in cost, time, taste), and tofurkey is unappealing (in taste, texture, appearance, concept...taste), and both are overplayed. And where's the fun in replicating what's been done before?

Thanksgiving is a time for tradition, yes, but it's also a time for creativity, for forging new paths, and for gimmick. So we abandoned our plans in favor of what was fresher (in both concept and flavor) and freer, with more room for play. While the all-vegetarian "ducken" has a history of its own, the idea was novel enough to give us excitement jitters (and buzzy enough to blindside us from the challenges to come).

So how did the "squashduckens" come to be?

Just as at Thanksgiving we remember a crucial (if somewhat fictional) part of our nation's history, so we will journey just a few weeks back in time to answer this question.

The story of how I came to nest squash within squash within squash (within squash within squash), and how Ali—much more reasonably—slipped cranberry within apple within pear within (you guessed it) squash is messy, complicated, and, I hope, soon to be inscribed in the Ye Olde Food52 Books of Yore.

Did we know how hard it would be? Did we anticipate just how intimate we would get with squash, how it would feel to lug upwards of 20 pounds of the stuff to the office from the Greenmarket, or the kind of looks we would get from our colleagues? Maybe we could have predicted these obstacles, but maybe it wouldn't be as fun that way.

The squashduckens were born, as so many Food52 ideas are, in our online chat system. We knew we wanted to make an all-vegetarian stuffed, layered, and nested Thanksgiving centerpiece, à la Dan Pashman, but we weren't committed to any particular vegetable (or variety of vegetable).

We tossed around the notion of putting a sweet potato inside a cored cauliflower inside a huge squash; of putting a red pepper inside an acorn squash inside a head of cabbage; and of nestling many, many tiny squashes side-by-side inside a massive Blue Hubbard.

And then we got so far off track that we weren't even sure we'd ever find our path again:

Thankfully, even terrible ideas can spark not-so-terrible ideas that one day might even become good ideas.

Ali ran with the notion of a fruitducken, thinking immediately of a sweet stuffed dessert made of easily-roasted fall fruits (pears, cranberries, and apples) cooked within a big squash (which is, technically, a fruit).

And the savory squashducken—squash nested within squash until the limit is reached—came from the sheer variety of squash at this month's farmers' markets. It seems that squash as small as Honey Nut are practically destined to be tucked inside a pumpkin as massive as a Long Island Cheese.

Once we had the theories in place, it was time to put them into practice. We both collected squash—Ali went to the market like a good student, whereas I collected specimens that were around the office as "decoration"—and we met on the weekend to conduct...

The First Test

Ali prepared with a diagram ( probably unnecessary, but we work how we work, right?).

Her creation was easy to assemble: Once the pumpkin and apple were carved, the pear cubed, and the crumble mixed, there was not much to it.

Meanwhile, I started on my own Frankenstein monster, carving and emptying the largest squash, then peeling and disemboweling the three smaller ones.

The work itself was labor intensive—the sloppiness and danger of making a jack-o'-lantern without the prospect of future candy—and the second-smallest squash was puzzling. Even though I'd identified it as a Sweet Dumpling, its insides smelled strangely sour. Was it even edible? Was it rotten?

But I was too excited that all of the squashes fit inside each other to be bogged down by "the details." With the hopes of making the whole thing taste good acceptable, Ali made a paste of garlic, ginger, and jalapeño, which we smeared over the top.

We placed both 'ducks on a cookie sheet, covered each with foil, and sent them into a 450° F oven, bidding adieu.

When we checked back about an hour later, there had been a great deluge. The pears, lemon juice, and water that Ali had added to her squashducken had generated an almost impossibly large amount of liquid, and it was seeping out of the bottom of the squash and onto the baking sheet.

We swiftly took the sheet tray out of the oven and performed emergency surgery, medevac-ing the squash to a ceramic baking dish where its ooze could be contained.

But despite that momentary disaster, Ali's fruitducken was ready just another hour or so later. Virtually unharmed, it was structurally sound enough that we were able to take nice slices, which steamed dramatically in the afternoon light. It was like we were watching a really boring movie about squash:

We were confused, yet proud. Amused, yet hungry. We both agreed that we needed to solve the liquid issue and increase the amount of spice and sweetener, but all in all, the test was a success. She also decided to make the dessert duckens in smaller squash to cut down on the cooking time even more. "I just threw together this spin on a turducken," Ali could (rightfully) say to guests when she would present them.

The same cannot be said, unfortunately, for the savory squashducken. After two hours in the oven, the squash was not even close to being finished. Having spent five hours at Ali's apartment, it was time for me to go home and leave my creation in her hands.

Several hours later, when the squash had been in the hot oven for the greater part of four hours, I received a photograph from Ali that nearly brought tears to my eyes. This is what it feels like to be a proud parent, I thought.

But the next photo, sent just a half hour later, taught me what it's like to be a disappointed, phone-call-from-the-police-at-3-A.M. parent.

The squash had been cooked at too high of a temperature, we theorized; while the outermost ring, which received the majority of the heat, overcooked and consequently deflated, the three inner squash were underdone and stood tall and raw even after so many hours in the oven.

But beyond that, the squashducken just didn't taste good. And that was probably because not all of them were edible. Oh, and I had neglected to put any salt, pepper, spices, or oil between the layers.

Clearly another test was in order.

The Second Test

While Ali was confident she could get her sweet squashducken right on the next try, I knew mine needed more development and headed into the office the next weekend. (What? You don't spend all of your free time with squash?)

For the second go-around, I didn't just make do with the rejected, questionably-edible squash lying around the office. This time, I headed to the Greenmarket to pick out as wide a range of squash as I could, and I made sure to ask the farmers to confirm that my selections were edible.

I peeled, carved, and emptied my squashes as I did last time, but now I had sharper utensils and was able to whittle away at both the outside and inside of the squash more effectively.

(I took a moment to consider if I should turn left and go straight to medical school.)

What's more, I had a whole new trick for making sure the inside squashes were cooked: I microwaved each one separately (ranging in time from 2 to 10 minutes) until flexible; I wanted them to be pliable enough that I could wiggle the flesh but firm enough that I wouldn't risk tearing them.

Cooking the inner squash most of the way through meant that they woudn't be raw even after the outer squash was cooked through. Plus, par-cooking slackened the squash, allowing me to wiggle them into squashes that were only the slightest bit bigger. (I think of this process as sliding beach balls into Neoprene sleeves.)

Sadly, after I tested to make sure the par-cooked squash fit snugly inside one another, the squash would not budge. I had no way to season between the layers, and so the hazelnut-sage pesto (a favorite from another Food52 squash recipe) that I made to flavor the squash was reserved for the outermost crevice and the very top.

I also added Parmesan and breadcrumbs—because if working at this company has taught me one thing, it's that Parmesan and breadcrumbs (...and cream...and anchovies...and salt) make most things taste better.

This time, I preempted any excess liquid leakage by assembling my squashducken within a huge cast-iron pot from the get-go. I baked at a lower temperature (350° F) to avoid #DeflateGate and after 1 hour and 45 minutes the outer squash was, I thought, fork-tender.

I let it cool slightly, then cut myself a small piece. Nope, still didn't taste good. I wondered about that outside squash, which wasn't palatable. Was it just a bad squash? Had it not been cooked long enough? Did I need to increase the amount of seasoning?

(Yes to all of the above.)

But beyond the taste of the squash, which I knew would be an easy-enough fix, I was concerned about the moat between the largest and second-largest squash. I had played it too safe, choosing a squash that dwarfed all the rest.

The crevasse had filled with oil from the pesto—a volatile situation that threatened the structural integrity of the 'ducken and made it impossible to remove from the pot.

For the last test—the one that would be in front of professional cameras and conducted on a weekday, with other people, including my bosses, around (!)—I would have to bridge the moat, either by adding cubed bread to function as oil sponges or by selecting my squash more carefully.

(I took another moment to consider if I should turn right and go straight to engineering school.)

The Third (& Final) Test

First, I got pumped.

Then, I went to the Greenmarket (...again). This time, I bought the biggest squash I could find that I was assured tasted good, and then I proceeded to carry it around to all the other stands like a toddler.

I sized up practically every squash at the market, picking up as many as I thought would make good 'ducken candidates.

At 8:30 A.M., I got to carving, scooping, and microwaving. This time, I rubbed the outside and inside of every squash with olive oil and pesto and sprinkled on crazy amounts of salt, pepper, smoked paprika, Parmesan, and breadcrumbs.

By 11:30 A.M., the squashes were secure, snuggled so tightly that there was no room for bread cubes and no risk of an oily cavity. I tented the pot with aluminum foil, set the timer for 1 hour and 45 minutes, and prayed.

In the meantime, Ali's fruitducken (so low-maintenance that you may have forgotten about it by this point) was assembled in fewer than 30 minutes.

It baked for 2 hours, after which it looked beautiful and smelled great. No surprises there.

My squashducken was also finished after 2 hours in the oven, but we weren't one-hundred percent sure how we'd get it out of the pot. (Just a minor detail!)

BUT WAIT: Kristen and Kenzi were up for the task. When the 'ducken had cooled slightly, Kristen tilted the pot towards a large serving platter and Kenzi held onto the baby, gliding it out gently. I held my breath and looked in the other direction.

Once the squashducken was on the platter, we celebrated:

We allowed the three little 'duckens to cool while we lined them up for their photo opp:

But then it was time for the real test: How would the slices look and, most importantly, how would they taste?

The massive squashducken, once slightly cooler, was beautiful to slice into, yielding pieces with six curved layers. The pesto and generous seasonings made the squash (all of which were creamy and edible this time around!) flavorful, and the paprika and olive oil had combined into a saucy liquid that helped keep everything moist.

Plus, it had helped to add the Parmesan.

The sweet squashducken tasted like roast squash, baked apples, and pear-cran crumble in one. Exactly what every indecisive person wants on Thanksgiving.

So, do you dare to ducken? It can be manageable or maniacal. That option we'll leave up to you.

The Squashducken Recipes

Ali's is the simplest squashducken around: Open up a squash, put a peeled and cored apple in it, fill the apple with cranberries, fill the area between the apple and the squash with a pear-cranberry topping, and top the whole thing with an oaty crumble. It asks less of you than a pie (and you've had pie before!). It is actually easy enough to make on a weeknight.

This 'ducken, on the other hand, is an epic undertaking. After many hours of wielding sharp tools and getting familiar with squash guts, your hands will turn oompa-loompa orange, you will make more squash than you ever thought possible, and you will probably finish 3 or 4 Clif Bars for sustenance.

But you will emerge triumphant. You will lower that mammoth squash onto the table as the centerpiece it's meant to be. Knock those mashed potatoes out of the way and turn on your victory song to play in the background. Provide your guests with roses that they can throw at your feet.

Because what's Thanksgiving without an epic, ambitious project to be grateful for? Rope your siblings, parents, and friends into helping you now. You can write it off as family time.

If you dare to ducken, let us know how it goes in the comments. Godspeed.