Warm Radicchio Salad with Squash and Caramelized Dates (beautiful for the holidays)

UPDATED 11/2023 :: She’s a beaut, no? Boasting the hot, glowy colors of a setting sun, this Warm Radicchio Salad is perfect for any fall or winter dinner table. There’s a cozy warmth to it, thanks to the addition of Indian Garam Masala, an optional addition and not make-or-break necessary, but lovely here. If you’ve got it, it works beautifully with the squash and sweet dates. It’s got this casual elegance to it, this salad, an attribute that I think is my favorite for any recipe – it’s a recipe sweet spot.

This warm radicchio salad holds its own on a dinner party table, but also works just fine as a great side dish or warm side salad on a weeknight dinner table.Kinda fancy, kinda not. Oh, and it’s incredibly, hopelessly delicious.

Tip and Tricks for Cooking Squash

You can use almost any hard-skinned fall or winter squash here (just not like, zucchini and summer squash, you know?). You don’t have to use butternut, it’s just what I’ve written the recipe for. But please feel free to do some squash riffing…

Types of Squash That Would Work Here:

• Delicata
• Butternut
• Acorn
• Kabocha
• Candy Roaster

As with all of my winter squash recipes, I’m going to have you pre-roast the squash here. Just throw it into a hot oven, let it sit there (directly on the rack) and roast away for about half and hour to 45 minutes. This will kickstart the cooking for you, and make it INFINITELY EASIER TO CUT.

This is a safety thing for me, if I’m being honest. A softened, pre-roasted squash is much easier to cut and work with than a totally raw one. And it’s also easier and faster to pan sear as well.

What You’ll Need For This Warm Squash and Radicchio Salad with Salty Balsamic Brown Butter

A simple-yet-mighty collective of flavorful ingredients combine into one of my all-time favorite salads to serve when the temperatures drop. Here’s the delicious cast of characters:

INGREDIENTS

Butternut squash – this also works with other types of squash. Buttercup, acorn, and kabocha (Japanese pumpkin) are my favorite subs here.

Cooking oil – I use olive oil, but any high smoke point, neutrally flavored oil will work beautifully. We’re searing and caramelizing the squash in a hot skillet, so we need and oil that is up to the task, and won’t burn on us.

Garam Masala – This gorgeous Indian spice blend brings all the cozy warm to this dish. It perfectly balances with the tart pomegranate seeds and the sweet dates. The bitterness of the radicchio is the perfect foil to the other flavors running all through this amazing warm radicchio salad.

Salt and pepper – Salting generously is encouraged here! The salt will draw out the spices of the Garam Masala and it will conjure maximum flavor from the squash as well.

Dates: This recipe calls for roughly chopped, pitted dates. I use Medjool most often in applications like this.

Pomegranate arils: They look like little glistening jewels atop a salad with the colors of a perfect sunset. Not to be over the top or anything, but she pretty.

Radicchio: This purple-hued, decidedly bitter chicory lettuce is one of my favorite things. It’s just so very self-assured, so far as a leafed thing can be. The flavor is bitter and strong and it really steals the show on any table. It’s best, however, when thoughtfully paired with other flavors that complement that bitterness.

Butter: You could use salted or unsalted in this Warm Radicchio Salad, up to you there. The butter will brown and then combine nicely with some balsamic vinegar into an unforgettable sauce with to drench the radicchio and squash.

Balsamic vinegar: There’s not a lot better than a salty, nutty balsamic brown butter. And this one is just the thing to really set this whole salad situation off.

How to make this Warm Radicchio Salad with Salty Balsamic Brown Butter

1. Preheat the oven to 375 degrees F. 
2. Place the unpeeled squash directly onto the oven rack and roast for 40 minutes. Allow it to cool until you can handle it, and then peel it (if desired, I often don’t), halve it lengthwise, scoop out the seeds and slice into discs/half moons.
3. Add 1 or 2 tablespoons of oil to a large nonstick skillet over medium heat. Add the squash to the pan, season well with salt, pepper, and (if using) the Garam Masala. Cook the squash on both sides until browned and crusty; about 6 to 8 minutes per side. They’re already well on their way, since we pre-roasted. So, just get things nice and tender, and beautifully brown. 
4. Arrange the radicchio on a large plate or tray (or individual plates) and top with the cooked squash. Add the butter to the skillet along with the dates. Allow the butter to melt and then brown, stirring occasionally as it does; takes about 5 minutes. 
5. When you can smell the nuttiness of the browned butter, add 3 more TBSP olive oil, the balsamic vinegar, and some salt and pepper to taste. Stir to mix and to get those dates crispy and caramelized. To finish this warm radicchio salad, spoon this warm vinaigrette over the squash/radicchio and top with the pomegranate seeds. 

If you like the looks of this autumnal Warm Radicchio Salad, you might also enjoy:

Garlicky Orange Chili Squash with Sage

Tunisian Harissa Chicken & Olive Skillet

Butternut Squash Galette with Feta and Sage

Creamy Cacio e Pepe Spaghetti Squash Boats

Lemon Cream Spaghetti with Hard Roasted Vegetables

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