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Bacon-Wrapped Acorn Squash with Maple & Chilli

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These Bacon-Wrapped Acorn Squash slices pair perfectly with a Sunday or Thanksgiving roast and make a delightful alternative to your usual pigs-in-blanket. The slices are glazed with maple syrup to enhance the squash’s natural sweetness and are paired with fresh chilli for a kick of heat and goat’s cheese for tang. This is one autumn and winter side dish you’ll treat yourself to again and again.

A white serving platter of acorn squash wrapped in smokey bacon, topped with white goats cheese and red chilli slices. there is a blue-grey linen napkin underneath the platter.

This Bacon-Wrapped Acorn Squash with Maple & Chilli dish is the second recipe in our 2020 Pinch of Pumpkin series! Have you signed up for our challenge yet and picked up your free copy of The Little Book of Pumpkin?

I’m beyond excited to share this recipe with you. When I was searching for inspiration on how to use this cutie, most of the recipes I found were either stuffed squash or roasted with brown sugar. Neither of which really inspired me.

What triggered this idea was actually Chris asking for pigs-in-blanket one Sunday as I was making roast. I didn’t have any cocktail sausages on hand, so I decided to wrap bacon around various vegetables instead, including a couple of butternut pumpkin slices. I think it’s fair to say we were both shocked by how good it was!

This Bacon-Wrapped Acorn Squash recipe was the result of a few more tests and this recipe will be accompanying my Sunday roasts and Thanksgiving feasts for YEARS to come. The combination of flavours is just… well, you’ll need to try it for yourself!

New to cooking with pumpkin?

Download your free copy of The Little Book of Pumpkin and learn how to identify and correctly use the 6 most common varieties of pumpkin to avoid bland, fibrous dishes.

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Why you’ll love this recipe

  • These Bacon-Wrapped Acorn Squash slices are a delicious alternative to traditional pigs-in-blanket. They pair perfectly with a Sunday roast or Thanksgiving banquet!
  • They’re sweetened naturally with a pure maple syrup glaze, which provides a lovely complement to the squash and contrast to the spicy chilli.
  • This recipe is small-batch, serving two to four people. However, it can easily be doubled to feed a larger crowd.
  • It’s such a simple and easy recipe to make; it’s the perfect place to start if you’re a novice to cooking with pumpkin and squash!
  • We’re using only 5 standard ingredients in this acorn squash side dish recipe, so it’s great for any day of the week.
a man in a black shirt serving a tray of bacon-wrapped acorn squash slices

How to roast pumpkin and squash

You’ll need:

  • 1 pumpkin or squash, deseeded and cut into 1-inch cubes
  • 2 large baking trays
  • Non-stick baking paper or silicone mats
  • 1 tbsp olive oil
  • Pinch of salt and pepper

How to roast pumpkin:

  1. Preheat the oven to 200ºC (400ºF).
  2. Line the baking trays with the non-stick paper or silicone mats.
  3. Toss the pumpkin well in the olive oil, salt, and pepper.
  4. Divide the pumpkin evenly between the two trays. Spread the pumpkin out so that there is enough room for air to circulate between each piece. You don’t want the pumpkin too crowded or it will steam instead of roast.
  5. Roast the pumpkin for 30-40 minutes, or until fork tender.
hot roasted acorn squash slices wrapped in bacon in a baking tray on a marble table with a bowl of goats cheese and red chilli slices on the side.

Ingredients in this bacon-wrapped acorn squash recipe

  • Olive oil: Perfect for roasting and glazing this dish.
  • Pure maple syrup: Combines with the oil to create the glaze and adds a lovely natural sweetness
  • Sea salt and black pepper: To season the glaze and the squash.
  • Acorn or carnival squash: Either kind will work for this Bacon-Wrapped Acorn Squash dish.
  • Smoked streaky bacon: Smoked bacon is delicious with the squash and maple syrup.
  • Red chilli pepper: To add a kick of heat that complements the sweetness of the dish wonderfully.
  • Goat’s cheese: Completely optional, but tastes fabulous with the squash, bacon, and chilli.

Can you eat the skin of acorn squash?

Yes, you can totally eat acorn squash skins! When they’re roasted, they soften and caramelise, making them completely edible.

a plate of Sunday roast chicken with greens and bacon-wrapped acorn squash on the side. there is a large plate of squash in the upper right corner.

How to make bacon-wrapped acorn squash

They may seem fiddly to prep, but I assure you that these Bacon-Wrapped Acorn Squash are actually super simple to do. In fact, I’d argue they’re even easier to do than pigs-in-blanket! Here’s how to make them (full instructions in card below):

  1. Deseed and slice the squash into 8 equal half-moon slices.
  2. Take a strip of bacon and wrap it around each piece of squash. Place them in a greased tray.
  3. Brush the squash slices with the maple syrup glaze and sprinkle over the chilli.
  4. Bake.
  5. Enjoy!
a plate of Sunday roast chicken with a side of mixed salad greens and bacon-wrapped acorn squash

Tips for making this recipe perfectly

  • If you’re baking this acorn squash side dish to accompany a Sunday roast, you can bake it on the bottom rack of the oven at the same time as the roast. It will likely take a bit longer to cook through, usually closer to 50 minutes.
  • For the smaller end pieces of squash, sometimes I find it easier to cut one slice of bacon in half and use the halves for wrapping instead of a full slice of bacon.
  • Keep an eye on the squash after the 35 minute mark if they still aren’t soft. The glaze has a tendency to burn quickly, so it’s best to watch it like a hawk.
  • I like this Bacon-Wrapped Acorn Squash quite spicy, but if you want a milder dish, simply remove the chilli once the dish is finished cooking and don’t top with the extra chilli slices.
These maple glazed Bacon-Wrapped Acorn Squash slices pair perfectly with a Sunday roast and are a great low-carb swap for pigs-in-blanket. Get the full recipe and other pumpkin recipe on naturallysweetkitchen.com via @naturallysweetkitchen

Looking for more refined sugar free pumpkin recipes?

Roasted Pumpkin Soup
Vegan Pumpkin Spice Cake
Pecan Pumpkin Sweet Rolls
Pumpkin Pie Protein Truffles
Pecan Pretzel Crusted Pumpkin Pie
Homemade Vegan Pumpkin Spice Lattes

If you make this recipe, let me know by snapping a picture and tagging me on Instagram @naturallysweet_kitchen. I love seeing your creations and sharing them in my Stories. Or let me know you love this Bacon-Wrapped Acorn Squash with Maple & Chilli recipe by leaving a comment and rating below!

New to cooking with pumpkin?

Download your free copy of The Little Book of Pumpkin and learn how to identify and correctly use the 6 most common varieties of pumpkin to avoid bland, fibrous dishes.

Includes two exclusive BONUS recipes!

By subscribing you agree to our privacy policy

bacon-wrapped acorn squash slices on a white plate topped with goats cheese and red chilli slices and a drizzle of olive oil
5 from 1 vote
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Bacon-Wrapped Acorn Squash with Maple & Chilli

These maple glazed Bacon-Wrapped Acorn Squash slices pair perfectly with a Sunday roast and are a great healthier swap for pigs-in-blanket.

Category Appetizer, Side Dish
Cuisine British
Keyword acorn squash appetizer, acorn squash side dish, bacon-wrapped acorn squash
Prep Time 15 minutes
Cook Time 45 minutes
Total Time 1 hour
Serves 8 slices
Author Amanda | Naturally Sweet Kitchen

Ingredients

  • 1 ½ tbsp olive oil
  • 1 tbsp pure maple syrup
  • Pinch fine sea salt
  • Pinch ground black pepper
  • 1 acorn or carnival squash
  • 8 slices smoked streaky bacon
  • 1 small red chilli pepper, sliced
  • 30 g mild goat’s cheese, for serving (optional)

Method

  1. Preheat the oven to 190ºC and very lightly grease a 28 x 23 cm (11 x 9 inch) baking tray with oil.
  2. In a small bowl, whisk together the olive oil, syrup, salt, and pepper until emulsified. Set aside.
  3. Trim the top off of the acorn squash and slice it in half lengthwise. Remove and discard the seeds. Turn the squash on its flat side and slice each half into 4 equal pieces.
  4. Wrap one bacon slice completely around each of the 8 pieces of squash.
  5. Place each bacon-wrapped squash slice in the baking tray, spread evenly apart. Brush the oil and maple syrup mixture over each piece of squash, being careful to get it on the sides and in all the crevices. Sprinkle over half of the red chilli slices.
  6. Bake the squash for 35-50 minutes, carefully flipping the slices half way through the cooking time. You’ll know they’re done when a fork can be easily inserted into the squash and the bacon is golden and crisp.
  7. Remove the tray from the oven and allow the slices to rest for 5 minutes before topping with the remaining fresh chilli and a sprinkle of goat’s cheese. Serve immediately.

Notes

  • For the smaller end pieces of squash, sometimes I find it easier to cut one slice of bacon in half and use the halves for wrapping instead of a full slice of bacon.
  • This dish is best served on the day it’s made.

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2 Comments

  1. I made these to give Sunday dinner a little pizzazz. Oh my they are a huge hit. My husband would like them every week now. So thanks for helping me get some variety into dinners and this will be a sure add to Thanksgiving this year.

    1. Amazing! I’m so glad you and your husband enjoyed the squash and want to make it again for Thanksgiving! The chilli and maple is just so good, isn’t it?

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