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    Whip & Wander » Recipes » sides

    Published: Feb 17, 2022 · Modified: May 17, 2022 by Jenni · This post may contain affiliate links.

    Roasted Acorn Squash with Calabrian Chili and Lemon

    This page may contain affiliate links. Please see my full disclosure policy for details.
    Jump to Recipe·Print Recipe
    a platter with yogurt, acorn squash, and kale
    a baking sheet with slices of acorn squash covered in calabrian chili oil
    a platter with roasted squash, italian kale, and greek yogurt
    a gold spoon resting in a dish of roasted squash, italian kale, and greek yogurt
    a large platter with roasted squash on top next to a set of gold serveware
    a golden spoon scooping up yogurt and kale with large slices of squash
    roasted squash with chilis on top of sauteed kale and yogurt

    Roasted Acorn Squash with Calabrian Chili and Lemon over a bed of kale and yogurt

    A bold and spicy side dish with a creamy base

    This Roasted Acorn Squash with Calabrian Chili and Lemon starts with wedges of acorn squash brushed with a mixture of spicy Calabrian chilis, lemon, and garlic oil, then roasted until their flesh is tender and their skins are caramelized. I love serving the roasted squash over a bed of thick Greek yogurt (or labneh cheese if preferred) and sauteed kale to help temper the heat from the chilis and make the dish feel extra hearty -- It's also a good excuse to add a loaf of crusty bread to help mop up every creamy, spicy, sweet, and acidic drop of this dish.

    a quadrant of 4 images showing sliced of acorns quash covered in chili oil and lemon

    What are Calabrian chilis and where can I find them?

    Calabrian chili peppers originate from the Calabrian region of Italy, sometimes referred to as “the toe of the Italian boot” as it is located in the southern part of Italy. The blood-red chili pepper offers a smoky and mildly fruity flavor with a moderate hot dose of heat. They are most commonly found in the US in oil-packed jars near the olives and other antipasti in the grocery store. You can buy jars of whole peppers which can be chopped for this recipe, or in jars of pre-chopped peppers.

    How spicy are Calabrian chilis?

    Calabrian chilis range from 25,000-40,000 Scoville Heat Units (SHU) on the Scoville Scale, which is used to help determine the heat level of chili peppers. To put this into perspective, a habanero pepper is rated as having a fairly high range of 100,000-350,000 SHU and a jalapeno pepper has a relatively low range of 3,500-8,000 SHU on average. Calabrian chilis fall somewhere in the middle of those two, on average, with a slightly milder range than Cayenne peppers, which are ranked at 25,000-50,000 SHU on average.

    I personally find Calabrian chilis to be assertively spicy and nice in small quantities, especially when paired with something sweet (acorn squash), something acidic (lemon juice), and something dairy-based (Greek yogurt), all of which helps to tame the heat slightly. They are lovely added as a supporting feature when a spicy kick would enhance the dish without overwhelming the flavor with heat. If you would like to lower the heat slightly, you can reduce the amount of Calabrian chili you use when making this recipe, but I would not serve this dish to those with especially mild palates.

    a hand using a gold spoon to spread yogurt over a platter

    kale ont op of a bed of greek yogurt on a platter

    How to prep an acorn squash for roasting

    1. On a sturdy cutting board, carefully trim both the stem end and the very top of the pointy end from the squash. Then turn the squash onto the now wide and flat flesh of the previous stem end and carefully slice the squash in half, from the top down.
    2. Using a spoon, scoop out the seeds from the center of both squash halves, then discard the seeds.
    3. Turn the squash flesh side down and slice into 1 ½-2 inch wedges. You can generally use the ridges of the squash as a guide, but it's not necessary to follow them.

    Can I eat acorn squash skin?

    Yes, you can eat the skin of an acorn squash after it has been roasted. While I would not recommend eating the skin prior to roasting, once it has been roasted, the skin becomes tender and easy to chew. However, if you do not prefer to eat the skin, it is easily removed post-roasting and should peel off fairly easily so you can skip the tedious task of peeling the skin before roasting.

    Roasted Acorn Squash with Calabrian Chili and Lemon ont op of sauteed lacinato kale and greek yogurt on a platter

    roasted acorn squash with calabrian chili on top of kale and yogurt

    What should I serve this dish with?

    Roasted Acorn Squash with Calabrian Chili and Lemon is a bold dish, so I prefer to serve it with simple main dishes like roasted chicken, fish, lamb, or steak. It also makes a lovely addition to meatless dishes such as crispy tofu or halloumi. Some of my favorite main dish recipes that would pair well with this dish are:

    • Grilled Skirt Steak with Avocado Chimichurri
    • Pressure Cooker Barbacoa Beef
    • Braised Leg of Lamb
    • Greek Lamb Meatballs with Tzatziki Sauce

    Looking for more side dish inspiration?

    If you prefer to serve this Roasted Acorn Squash with Calabrian Chili and Lemon alongside other shareable side dishes, it would make a lovely addition for tapas or a mezze spread. Some of my favorite side dish recipes that would pair well with this dish are:

    • Crispy Cauliflower with Romesco and Feta
    • Baked Feta with Green Olives and Figs
    • Pressure Cooker Artichokes
    • Olive Tapenade served with Easy Labneh Cheese
    • Za'atar Roasted Carrots with Labneh, Honey, and Pistachios
    • Roasted Greek Potatoes with Whipped Feta
    • Roasted Brussels Sprouts with Honey Sriracha Sauce

    a paltter of Roasted Acorn Squash with Calabrian Chili and Lemon resting next to gold serving utensils

    a gold serving spoon dipping into yogurt with kale and sqaush on top

    What tools do I need to make this recipe?

    • A cutting board
    • A chef's knife
    • A kitchen scale -- OR -- measuring cups (for less precise measurements)
    • Measuring spoons
    • A small mixing bowl
    • A fork
    • A basting brush
    • A baker's half sheet lined with parchment paper
    • A large skillet
    • A wooden spoon or spatula
    • A spoon or spatula (to spread the yogurt)

    Are you looking to upgrade to your cooking tools or replenish your pantry? Check out my kitchen tools shop page and pantry staples shop page to find my must-have kitchen tools, pantry items, and other Whip & Wander favorites.

    a gold serving utensil resting in a dish of Roasted Acorn Squash with Calabrian Chili and Lemon

    a gold serving spoon dipping into yogurt under roasted squash

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    Roasted Acorn Squash with Calabrian Chili and Lemon over a bed of kale and yogurt

    Roasted Acorn Squash with Calabrian Chili and Lemon

    ★★★★★ 5 from 1 review
    • Author: Whip & Wander
    • Prep Time: 10 minutes
    • Cook Time: 25 minutes
    • Total Time: 35 minutes
    • Yield: 8 servings 1x
    • Category: Sides
    • Method: Oven / Stovetop
    • Cuisine: Mediterranean
    • Diet: Vegetarian
    Print Recipe
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    Description

    This Roasted Acorn Squash with Calabrian Chili and Lemon starts with wedges of acorn squash brushed with a mixture of spicy Calabrian chilis, lemon, and garlic oil, then roasted until their flesh is tender and their skins are caramelized. I love serving the roasted squash over a bed of thick Greek yogurt (or labneh cheese if preferred) and sauteed kale to help temper the heat from the chilis and make the dish feel extra hearty -- It's also a good excuse to add a loaf of crusty bread to help mop up every creamy, spicy, sweet, and acidic drop of this dish.


    Ingredients

    Scale

    For the roasted acorn squash:

    • 1 large acorn squash (about 2 ½ lbs)
    • 1-2 tablespoon Calabrian chilis in oil*, finely chopped (for very hot use 2 tbsp, for slightly less hot use only 1 tbsp)
    • 1 tbsp lemon juice (I prefer Meyer lemon if available)
    • 2 tsp lemon zest
    • 1 tbsp garlic-infused olive oil -- OR -- 1 tablespoon olive oil + 1 clove minced garlic)
    • ½ tsp Kosher salt
    • ¼ tsp cracked black pepper

    For the sauteed kale and yogurt base:

    • 1 bundle (about 5 oz) of Lacinato kale, freshly washed, deveined and chopped
    • 1 tbsp olive oil
    • ½ tsp Kosher salt
    • 16 oz thick Greek yogurt (may swap for labneh cheese if preferred)

    Instructions

    For the roasted acorn squash:

    1. Preheat your oven to 400 degrees F / 205 C. Line a baker's half sheet with parchment paper and reserve to the side.
    2. On a sturdy cutting board, carefully trim both the stem end and the very top of the pointy end from the squash. Then turn the squash onto the now wide and flat flesh of the previous stem end and carefully slice the squash in half, from the top down.
    3. Using a spoon, scoop out the seeds from the center of both squash halves, then discard the seeds.
    4. Turn the squash flesh side down and slice into 1 ½-2 inch wedges. You can generally use the ridges of the squash as a guide, but it's not necessary to follow them.
    5. Transfer the wedges to the reserved baking sheet, flesh side down (other side of flesh exposed), and reserve to the side.
    6. In a small mixing bowl, combine the Calabrian chili, lemon juice and zest, garlic-infused olive oil (or olive oil + minced garlic), and salt. Brush the mixture over the tops of the squash flesh, ensuring that the chilis are dispersed reasonably evenly and the squash has been fully brushed with the chili and garlic oils.
    7. Sprinkle the tops with cracked black pepper and transfer to the oven. Roast for 25 minutes or until the squash flesh is fork-tender and the skin has lightly caramelized. Reserve to the side until ready to assemble.

    For the sauteed kale and yogurt base:

    1. In a large skillet over medium-high heat, add the olive oil. Once shimmering, add the kale and stir to combine. If you have just washed your kale and it is slightly damp this will help the kale steam slightly as it cooks resulting in a more tender green. If you have prewashed your kale and it is now dry, I like to add 1-2 tablespoon of water to the pan at this time to help the kale steam and tenderize.
    2. Season with salt and continue to stir regularly until the greens are soft and tender.
    3. On a platter, spread the Greek yogurt (or labneh cheese) down in a thick layer. Top with sauteed kale, then top with the reserved roasted acorn squash.

     


    Notes

    Nutritional information on Whip & Wander is provided as a courtesy and is approximate only. We cannot guarantee the accuracy of the nutritional information given for any recipe on this site.

    *Calabrian Chilis: You can buy jars of whole peppers which can be chopped for this recipe, or in jars of pre-chopped peppers.


    Nutrition

    • Serving Size: ⅛th of recipe
    • Calories: 131
    • Sugar: 2 g
    • Sodium: 178 mg
    • Fat: 5 g
    • Saturated Fat: 1 g
    • Carbohydrates: 17 g
    • Fiber: 2 g
    • Protein: 7 g
    • Cholesterol: 7 mg

    Keywords: acorn squash, calabrian chili, lemon, kale, yogurt, labneh

    Did you make this recipe?

    Tag @whipandwander on Instagram and hashtag it #whipandwander

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    Comments

    1. Brooke says

      December 12, 2022 at 7:14 pm

      This recipe was DELICIOUS. The contrasts of the yogurt/kale/squash worked SO well together. I especially loved what the yogurt brought to the dish. Really elevated it compared to a normal side. I will definitely make this again!

      ★★★★★

      Reply

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