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Cinnamon Maple Squash & Pink Radicchio Salad

This Cinnamon Maple Squash & Pink Radicchio Salad will be your new favorite winter side dish! We’re pairing roasted Delicata with warming spices and serving gorgeous radicchio greens with quinoa, walnuts & orange-tahini dressing for a well-rounded meal.

overhead view of cinnamon maple Delicata squash salad

Today’s salad is a feast for the eyes, literally. I had so much fun photographing this lovely bitter green, but the taste is just as enjoyable. The cinnamon-maple caramelized squash really offsets the entire dish in the best way, so let’s get into the details.

What is radicchio rosa?

Radicchio rosa is a leafy vegetable from the chicory (bitter green) family. The “rosa” comes from its bright pink hue. If you have never eaten regular radicchio, you have likely seen it at the grocery store. The most common varietal has a tightly packed head with deep purple and white striations.

head of radicchio rosa on a table

How to Make a Perfect Winter Salad

Salads and winter can go hand in hand! Here are the key elements you need for a satisfying and healthy recipe:

  1. Hearty base green. Lighter lettuces and baby spinach are not the best option for colder days. For a great winter salad, you want to use something thick with chew that will stand up to a viscous dressing.
  2. Protein-rich grain. For staying power in chilly winter months, the addition of a textural grain (or a gluten-free seed, like quinoa) is essential for satiation. Other good options are buckwheat, emmer/farro, and short grain brown rice.
  3. A roasted vegetable. I really crave warming veggies in the winter – this makes sense as it falls in line with the seasonality of produce! Cucumber and tomato are both things I’d rather postpone until a heat wave. Roasted broccoli, sweet potato, carrots, and (of course) squash are comforting and substantial enough for winter weather dining.
  4. Nuts or seeds. These provide texture plus more plant-protein. I use nuts in warmer months as well, but something about the contrast of a silky roasted vegetable + the sharper crunch of a toasted seed is really appealing in cool weather. Pistachios, almonds, and walnuts are some of my favorites.
  5. A thick dressing. I tend to avoid vinaigrettes in winter and stick to dressings with more heft – typically those with a seed- or nut-butter base (as opposed to vinegar and oil). Peanut butter and tahini are two of my current favorites! They transmit flavor beautifully and really makes things satisfying.
  6. Something sweet. A slightly sweet garnish really takes a winter salad to “excellent” territory. I believe it is what contrasts with the richer, sometimes bitter flavors we’re getting from the greens and grains. My favorite option for a pop of sweetness in a salad is a chopped Medjool date. Fresh or dried winter fruits (such as oranges, cranberries or raisins) or candied nuts are all welcome.

Swaps for Radicchio Rosa in This Recipe

Pink radicchio is sadly difficult to find in most grocery stores – I’ve only ever seen it at a farm market. Regular radicchio (the purple kind) would be a nice substitute that you can buy pretty much everywhere. A combination of dandelion greens and frisée would also be nice. When I doubt, feel free to use curly or Lacinato kale.

More Winter Salads

Herby Quinoa Salad with Go-To Tahini Dressing (try swapping blueberries for apples)

Arugula Fennel Salad

Kale Caesar Salad with Crispy Chickpeas (my favorite chickpea cooking method)

More Winter Squash Recipes

Quinoa-Stuffed Honeynut

Spaghetti Squash Lasagna Boats

Spaghetti with 12 Cloves of Garlic (featuring Delicata)

Sesame Miso Ramen

Thai-Inspired Pumpkin Curry

I hope you love this Pink Radicchio Salad Recipe! Please be sure to leave a rating and a comment if you give it a try.

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overhead view of cinnamon maple Delicata squash salad

Cinnamon Maple Squash & Pink Radicchio Salad

  • Author: Emily
  • Total Time: 30 minutes
  • Yield: 6 servings 1x
  • Diet: Vegan


This Cinnamon Maple Squash & Pink Radicchio Salad will be your new favorite winter side dish! We’re pairing roasted Delicata with warming spices and serving gorgeous radicchio greens with quinoa, walnuts & orange-tahini dressing for a well-rounded meal.  


Units Scale

For Cinnamon-Roasted Squash:

  • 1 medium-sized Delicata squash
  • 1 TBS avocado oil
  • 1 tsp cinnamon
  • Salt and pepper, used throughout

For Orange-Tahini Dressing:

  • 4 TBS tahini paste, as runny as possible
  • 1 tsp orange zest, from one orange (optional)
  • 2 TBS orange juice, freshly squeezed if possible
  • 1 tsp olive oil
  • Pinch of salt

For salad base:

  • 1 cup quinoa or farro, cooked
  • 1 head of rose radicchio, or other bitter green, washed and separated from the head
  • 1/4 cup walnuts or pistachios, chopped
  • 1/4 cup flat leaf parsley, chopped
  • 1/4 cup dates, chopped (optional)


  1. Begin by roasting squash. Preheat the oven to 400 degrees F and lightly oil one sheet pan. Slice Delicata in half and use a spoon to remove the seeds, setting aside to compost or roast later. Slice each half of the squash into 1/2-inch thick semicircles. Add to the baking sheet and toss with oil, cinnamon, and a dash each of salt and pepper. Stir to ensure squash is fully coated and spread out on the pan so the pieces are not touching. Roast for 20 minutes, flipping at the halfway point to ensure the squash cooks evenly. Set aside once done.
  2. While squash is roasting,  mix all ingredients for dressing in a small bowl, using a fork to whisk evenly. Add a splash of water to ensure things come together. It should be thick but pourable. 
  3. Prepare your quinoa or farro if using, according to package directions. 
  4. To assemble salad, lay radicchio leaves on a large platter. Evenly add cooked grain of choice across the leaves. Sprinkle on Delicata squash, then walnuts, parsley and dates if using. Drizzle dressing on top (you may not need all of it, so reserve some for another use), and enjoy! This salad will hold up pretty well in the fridge for a few days (radicchio does not really wilt), but be sure to reheat before having the leftovers. 
  • Prep Time: 10 minutes
  • Cook Time: 20 minutes
  • Category: Salad
  • Method: Baking
  • Cuisine: American


  • Serving Size: One sixth of recipe
  • Calories: 171.5 calories
  • Sugar: 2.1 grams
  • Sodium: 75 milligrams
  • Fat: 11.1 grams
  • Saturated Fat: 1.4 grams
  • Unsaturated Fat: 9.7 grams
  • Trans Fat: 0 grams
  • Carbohydrates: 15.4 grams
  • Fiber: 3 grams
  • Protein: 4.5 grams
  • Cholesterol: 0 milligrams

Keywords: radicchio, quinoa, squash

Portrait of Emily Meyers, founder of Garlic Head

About the Author

Emily (Frigon) Meyers is the founder of Garlic Head, a plant-based recipe website for all eaters who want to easily, affordably, and sustainably incorporate more vegetables into their diets while saving time and money. She is a lifelong vegetarian and 10+ year vegan. Garlic Head does not focus on labels - it focuses on creating food that everyone can enjoy.

Emily earned a certificate in Plant-Based Nutrition from Cornell University along with degrees in Economics, Spanish, and Global Sustainability from the University of Pittsburgh. She has been featured on numerous podcasts and websites including The Food Institute, VegNews, Buzzfeed, and the Boston Globe.

Meet Emily here.

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