acorn squash wellington with pistachio pesto and goat cheese, roasted broccoli and creamy cauliflower “mashed potatoes”

I’m on a use-what-you-have kind of a kick lately, and what I have is a recent love affair with fennel seed. And acorn squash. And my pistachio pesto.

What to do… what to do…

I looked online and could not find one instance where acorn squash was used as a Wellington – Butternut squash yes, but not acorn squash so, I decided to try this myself. It did NOT disappoint. If you love something that looks impressive like it took all day – and a grandmother’s recipe – to make, a Wellington is the way to go. If you’re interested in some other options, my menu has an entire link dedicated to these puffy pockets (use the link below)


You Will Need:

  • Puff Pastry
  • Eggs (one egg for two wellingtons)
  • Goat Cheese (plain, fresh)
  • Grated Parmesan
  • Pistachios (shelled is preferable to save time)
  • Fresh Spinach Leaves
  • Dried Basil
  • Fennel Seed
  • Salt, Pepper
  • Olive Oil
  • Toasted Sesame Seed Oil (optional)
  • Sour Cream
  • Cauliflower Florets
  • Broccoli Florets
  • Rolling Pin (bottle of wine)
  • Food Processor (can be mini or blender)
  • Parchment Paper (or aluminum foil)

Prepping your squash is simple – much like butternut, the hardest part is getting into the thing in the first place. Always cut along it like you would an avocado stopping at the hard end and then going again along the other side till you can put the knife down, hold each end of the acorn and pull it apart.

Take out the seeds and pulp and discard. Place the acorns in a casserole dish or on a baking sheet.

Start to stab the acorns all over with a knife. This will help steam them but most importantly, get all the gorgeous oil and flavoring in them while they cook.

Pour the oil on first: liberally, then the salt, pepper and basil. You can always add more later but you’ll need quite a bit now.

Pop them in the oven on 400 degrees for 50 minutes.

Next thing you’ll want to do is prep your broccoli to be roasted. Take your florets and pour them out on parchment paper or aluminum foil. Drizzle with the toasted sesame seed oil (or olive oil) – no need to stir them, and pop them frozen or fresh into the oven on 400 for 40 minutes when the squash is done. If you have room in your oven to do both the squash and the broccoli go ahead – otherwise, they can cook afterwards. You can prep the rest of the meal in the meantime.

Get your cauliflower steaming: Again, if you can, and there’s room, put them in the oven on a separate baking sheet for the same temperature for 40 minutes. If you can’t, you’ll need to steam them. You can achieve this by placing the florets in a microwave safe bowl with some water in the bottom and cover the top while microwaving till the heads can be pierced with a knife. We use a steaming container.

Same concept with the water in the bottom and microwaving. You can also use a bamboo steamer, or your preferred method. We just want them soft so they can be blended. You don’t need to drizzle any oil on them or season them at all.

While those steam (or roast) take your puff pastry out of the freezer.

You’ll see there will be two packets per box – you’ll use one packet per two people. Take out what you need and do not try to unfold them. They need to stay folded until they defrost or they’ll break apart.

When the squash is done, take them out to cool just long enough so that you to handle them.

While they cool, you can quickly make your pistachio pesto.

In a blender or food processor, add two handfuls of spinach leaves, two handfuls of pistachios, some salt, pepper and about a tablespoon / tablespoon and a half of dried basil. On top, add a bunch of grated parmesan and add enough olive oil that everything emulsifies.

Taste and see if you’d like more salt.

This is the creamy texture you’re looking for:

Your squash will be cooled now, go ahead and scrape out the insides without going down all the way to the “peel” and put it in a separate bowl to take to your puff pastry.

The pastry should be defrosted by now, so go ahead and open it. You’ll see two pieces of paper, discard that and open all the way.

Take your rolling pin (or bottle of wine) and roll it out so that it’s flatter and larger – still keeping the edges as straight as you can. Basically wanting to add about an inch or more on each side in size.

Then slice right down the middle with your knife.

Take some of your pistachio pesto and plop it on each bottom end of the pastry (you’ll see where I got a bit close to the edge with the one on the right; I corrected that and pushed it back up. You need a definite edge for sealing later).

Add heaps of your squash.

Take your goat cheese and pull pieces off and tuck them within every part of the squash you can fit. Not the whole large container of goat cheese, of course. I think I used a third between the two of these wellingtons. If you bought the smaller sized goat cheese, use a half per Wellington.

Take some spinach leaves, rip off their stems so they don’t poke through the pastry.

Top your piles with the spinach.

Take your egg, crack it into a bowl and whisk it. Take your finger or a pastry brush and coat all the edges.

Then, take each end of pastry and fold it over.

Fold each end up onto itself – it will be messy but it’s okay…

Take the tongs of a fork and crimp each side “closed”. Again, chance this will be messy but it will end up fine.

Grab your wellingtons and place them on parchment paper (or aluminum foil) in a baking sheet or casserole dish. Take your knife and make three small slits in each top so the steam can release.

Take the rest of your egg wash and coat the entire Wellington. This will create a gorgeous crispy brown finish.

If you’re not yet ready to cook these off (and I wasn’t; I made these a day ahead), you can place these covered in the fridge and cook them off the next day.

If you ARE ready, they’ll go in the oven on 400 degrees for 22-25 minutes. I cooked these for 23 minutes – but you definitely want to see the crispy brown tops – however long you choose between those times.

Your broccoli and cauliflower will absolutely be done by now. Take your broccoli and drizzle olive oil, top with salt and pepper (to taste) and if you need to keep them warm, place them (after being seasoned) in the oven on 160 degrees for as long as you need. Make sure to stir them after seasoning them.

Your cauliflower can be now put in batches in your food processor or blender. You will add as much cauliflower as will fit (making sure they were fork tender first), topping with a tablespoon of fennel (I made these in two batches, a tablespoon a batch so make sure you use the amount appropriate for how many times you need to do this), two tablespoons of grated parmesan, some salt and pepper and two tablespoons of sour cream with a one count of olive oil. You may need more oil depending on how large the amount of food per batch you’re blending.

Blend and taste.

See if you want to add anything. My FAVORITE thing obviously was the taste but also, the flecks of fennel within the mashed cauliflower. That’s one of the reasons it was so important this was fennel seed. The look of the flecks really paired well with the Wellington which looks so old world to me… It’s like asking for French vanilla ice cream and seeing the flecks of vanilla…

When you go to plate, place a clump of cauliflower down on the plate, the Wellington on top and some broccoli to the side.

The pastry is so flaky and the inside so creamy from the squash… The first thing you’ll taste is the pesto as we put it on the bottom. The goat cheese has a nice tang to it which complements both the squash and the cauliflower. The broccoli has a nutty flavor that works well with the fennel and the pesto… It’s a vibrant impressive plate that has no meat and fun flavors. It’s my sort of, bon voyage to winter.

And also, now – I can say I’ve seen an acorn squash Wellington. Why not!?

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