Like the Crispy Chicken Ballotine, this recipe is another Keith discovery. In fact, he made both for me on the same night. Yes, I am a VERY lucky girl.
The second time we had it, we decided to riff on the original recipe by Melissa Clark (one of our favorite recipe resources), swapping in maple syrup for honey, plain yogurt for buttermilk, walnuts for pecans and smoked paprika for chili powder. Both ways were delicious, but I’ll have to give the nod to maple syrup over honey.
If you’re new to delicata squash, this is a great way to introduce yourself. It’s absolutely my favorite winter squash. In fact, most of the time, we roast it and eat it plain; it’s so sweet it needs nothing: no salt, no sugar, no butter – nada. However, it dresses up beautifully. Roasting it with maple syrup, smoky paprika and salt gives it incredible depth and complexity. Then tossing it with peppery arugula, bitter-crisp raddichio, buttery toasted walnuts and creamy, tarragon-kissed dressing, well…no need to imagine, try it instead!

Roasted Delicata Arugula & Raddichio Salad w/ Creamy Tarragon Dressing
Ingredients
- 2 delicata squashes
- 2 tablespoons maple syrup
- 1 ½ teaspoons kosher salt divided
- ¼ teaspoon smoked paprika
- 6 tablespoons extra-virgin olive oil divided
- 1/3 cup plain full-fat yogurt
- 2 teaspoons fresh lemon juice
- 2 teaspoons finely chopped tarragon
- 1 small clove garlic minced
- 1 small head radicchio cored and thinly sliced
- 5 ounces arugula
- 1/3 cup toasted walnuts chopped
- 2 green onions thinly sliced crosswise
- salt and freshly ground black pepper
Instructions
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Preheat oven to 425°F.
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Line a rimmed baking sheet with parchment paper.
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Cut one delicata squash in half lengthwise. Scrape out the seeds and slice into 1/2-inch half-moons. Repeat with remaining squash.
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In a large bowl, whisk together maple syrup, 3/4 teaspoon salt, smoked paprika and 2 tablespoons olive oil, add squash slices and toss to coat evenly. Transfer to prepared baking sheet, spreading into a nearly single layer. Roast, tossing occasionally, until tender and golden brown, 25 to 30 minutes. (Don't roast so long that the squash lose their shape.)
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Meanwhile, in a small bowl, whisk together yogurt, lemon juice, tarragon, remaining 3/4 teaspoon salt and garlic. In a steady stream, whisk in remaining 4 tablespoons olive oil; whisk until emulsified.
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In a large bowl, combine radicchio, arugula, squash, walnuts and green onions. Pour in dressing and toss to coat; season to taste with salt and pepper. Serve.
What a beauty! Never heard of this beautiful Delicata Squash and this indeed would be a great first introduction. Go Keith and hooray of maple syrup! That first photo is fantastic too BTW. 🙂
This salad is such a beauty and I agree 100% – delicata squash is absolutely the best! Roasted is my favorite way to go with it too. We recently had a guest over and I made a salad with roasted delicata for her on the first night she arrived…not only did she request it for another meal, but she asked for the recipe! I think it’s high up on everyone’s list, and for such good reason. And I am also with you on maple syrup! 🙂
I love it! I think for most people, it just takes one try to fall in love with delicata squash. Thanks, sweet friend!
I love delicata squash – soooo good! This is such a great way to utilize it. And I’m with you on the maple syrup – I love it in a nice salad dressing like this! You are definitely one lucky gal, but Keith is really lucky too! 😉 <3
Thank you, Beeta!
What a lovely salad! The combination sounds wonderful!
Looks beautiful! So fresh, colorful and I’m sure delicious! Will definitely try it! Love the photo!
Thank you so much, Mira!
I’m going to have to look it up to see if we can get delicata squash in winter. It sounds like the perfect kind of squash to eat. And yum to this creamy dressing! 😀
Thanks, Lorraine. It’s definitely a dressing that would work on many different salads – love that little licorice (tarragon) kiss!
Yes, you ARE a lucky girl! This is a stunning recipe with stunning photos to match.
Thank you, Helen! xo
This looks so fresh and delicious! I need to make more delicata squash in my life.
You and me too! 🙂
Oh, Marissa! This looks and sounds wonderful! I couldn’t agree more about the incredible combo of squash, maple syrup, and paprika (sometimes I use a pinch of cayenne.) Arugula – favorite green. Raddiichio – love it for the bitter component. Tarragon dressing – fabulous licorice flavorings. Together create a wonderful balance of flavor. Beautifully done!
oooh, I like how you think – a little pinch of cayenne would be a great addition…thanks, Kathleen! xo
Hi Marissa! This, along with the chicken and your wonderful husband makes YOU one lucky gal! Of course, he is a pretty lucky guy to have you! You swapped yogurt for the buttermilk, but in the body of the recipe you said to add the “buttermilk” dressing – which do you prefer? I am definitely making this and the chicken soon! 🙂
So sweet, Dorothy, thank you! And I must have had buttermilk on the brain – it should just say ‘dressing’, or ‘yogurt dressing’ – though buttermilk works well too – so whatever you prefer or have on hand. 🙂