Winter squash is roasted, filled with a sweet “candy” mixture, drizzled with maple syrup and roasted again to combine flavors. Â This paleo and vegan roasted squash recipe is perfect as a sweet side dish for the holidays, or a dessert!
We just can’t get away from winter squash, can we? Â Maybe if I had the discipline to stop buying squash at every grocery trip, the recipes would stop too. Â Soon, I promise.
But for now, we’re getting cozy and sweet with my two of my current obsessions – winter squash and maple syrup. Â Oh, and pecans and dates, too, but they’re generally a year-round staple for me.
As is maple syrup, I now realize, but details, really. Â Let’s get back to the squash and see what’s going on here before we get the oven started!
As I mentioned above, I go a little wild at the grocery store with squash this time of year. Â It’s my favorite way to do the whole seasonal-eating thing which I normally don’t pay much attention to (oops!)
My favorites are butternut, delicata, and acorn squash, but I also like to buy those fun, colorful “carnival” squash, which sort of look like small acorn squash but a whole lot brighter and “stripy” for lack of a better term.
They look like acorn squash with stage makeup, or perhaps they just look like squash at a carnival, hence the name. On the inside, they have a pale color similar to a delicata, and in my opinion the taste is a cross between acorn and delicata. Â Shall we move on?
Yes, so for this particular recipe, you can use any winter squash you want, as long as it’s small.  Don’t worry, if your squash is TOO small, just make sure you have a third and roast that one, too.  Just look for the smallest, most happy squash in the store and buy a few of those, for best results 🙂
And by happy squash, I guess I mean the squash that makes YOU the most happy when you see it. Â Squash doesn’t have feelings, people who look at squash do.
As for the filling, I was inspired by two things – 1.) Maple syrup (see my last post for details and 2.) My favorite sweet Thanksgiving side dish – “candied” sweet potatoes.
Let’s face it, anything you can do with sweet potatoes, you can do with winter squash, perhaps even better (AKA anything you can do I can do better.) I’m not going to say this recipe trumps my candied sweet potatoes – not nice to play favorites with recipes 🙂
What I AM saying is that this recipe is insanely delicious. Â It’s sweet – so sweet that it really could be a dessert, because it legitimately tastes like candy.
The caramelized roasted squash combined with chopped dates, coconut, pecans and maple syrup is basically the best combination ever, period. Â I actually want to try making cookies out of this mixture, it’s just that good!
Anyway, I think we’re all ready to start – pick out your happiest squash and turn the oven on – let’s go!
“Candied” Maple Roasted Squash {Paleo & Vegan}
"Candied" Maple Roasted Squash {Paleo & Vegan}
Winter squash is roasted, filled with a sweet "candy" mixture, drizzled with maple and roasted again to combine flavors. This paleo and vegan roasted squash recipe is perfect as a sweet side dish for the holidays, or a dessert!
Ingredients
Squash:
- 2 small winter squash *See note
- 2 tbsp Melted coconut oil and sea salt for roasting
Filling:
- 3/4 cup chopped pecans
- 1/3 cup unsweetened flaked coconut
- 4-5 medjool dates pitted and chopped
- 2 Tbsp coconut oil melted
- 3 Tbsp pure maple syrup divided
- 1/2 tsp cinnamon
- 1 tsp pure vanilla extract
- 1/4 tsp fine grain sea salt
Instructions
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Preheat your oven to 425 degrees. Cut both squash in half lengthwise and scoop out seeds and strings with a spoon. Brush inside of squash with melted coconut oil and sprinkle with sea salt.
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Place the 4 squash halves face-down on a baking sheet, lined with aluminum foil if desired. Roast for 25 minutes, or until top is soft. Larger squash will require longer roasting times. Once done, remove from oven to fill, but keep the oven on for the second roasting.
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While squash roasts, mix all filling ingredients together in a bowl, except only add 1 1/2 tbsp maple syrup - leave the rest for drizzling
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Turn over roasted squash and fill evenly with pecan mixture. Since it’s a rich filling, we’re not stuffing it to the brim - about 1/4 cup filling per squash half for small squash.
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Once filled, carefully drizzle remaining maple syrup over the tops of the squash (concentrate on the squash, not filling, since it's already sweet)
Place baking sheet in the oven again and bake for another 10-15 minutes until toasty. Remove from oven and serve warm, as a sweet side dish or dessert. Cut into pieces for smaller servings if desired. Serves 6-8 as a side.
Recipe Notes
*Acorn, carnival, butternut, delicata would all be good, I used carnival squash. One larger squash can be used in place of two small, but will need to roast longer.
What I Used To Make My “Candied” Maple Roasted Squash:
Want More Paleo Winter Squash Recipes? Â Try one of these!
Roasted Butternut Squash Hash with Apples and Bacon {Whole30}
Sausage Apple Cranberry Stuffed Acorn Squash {Whole30}
Butternut Squash Stuffing with Sausage, Apples and Cranberries {Whole30}
Roasted Butternut Squash Salad with “Buttermilk” Dressing {Vegan, Whole30}
Caramelized Onion Sausage Apple Stuffed Acorn Squash {Whole30}
Beef and Bacon Stuffed Delicata Squash {Whole30}
Tell Me!
What’s your favorite sweet side dish?
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This looks so good that I want to make it but don’t have any dates. Would this taste good with dried cherries in place of dates?
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This is so good!!!! It tastes exactly like pecan pie!!
Candy made by grilled Maple Maple grapes are delicious and attractive. I really like this dish.
These were delicious! Reminds me of my grandmother’s acorn squash with brown sugar and butter but honestly tasted better?.
Excellent! Super sweet. I only put in a tablespoon of the maple syrup into the mixture and didn’t pour any on the squash. I might even put a little less into the mixture and continue to skip putting it on top of the squash. I did just two dates.