I’ll admit, salad isn’t always my first choice for a meal—but once I discovered how to make GOOD salads packed with interesting flavors and textures, that all changed. This Kale & Squash Winter Salad has become one of my favorites because it’s delicious, vibrant, and super customizable to whatever you have on hand!

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Things to Consider

Greens/Base:

  • I use kale because it holds up well in the fridge (perfect for meal prep).
  • Substitutes: Arugula, romaine, or even farro/grains for extra heartiness.

Roasted Veggies:

  • Any squash works here (bonus: save the seeds ti add extra crunch!).
  • Sweet potato is a great alternative.

Additional Veggies/Fruits:

  • Add 1-3 for variety of your favorite veggies and fruits.  
  • My favorite: apple & fennel—individually great, but even better together!

Toppings:

  • Crunchy, salty, sweet—go wild!
  • Try toasted dates (sautéed in butter = new obsession) and shaved manchego or parmigiano cheese…an UMAMI flavor bomb

Dressing:

  • Homemade is best (and easy), but a good store-bought also works.

Ingredients

Salad Ingredients:

  • 1 bunch Tuscan/Dino kale (ribs removed, thinly sliced)
  • 1 small squash (butternut, honeynut, or koginut), peeled, seeded, and cut into 1-inch cubes
  • 1 apple, thinly sliced
  • 1 small fennel bulb (top removed, thinly sliced)
  • 5 dates, cubed
  • ¼ cup shaved manchego or parmigiano cheese
  • Olive oil
  • 1 tbsp butter
  • Salt and pepper

Dressing Ingredients:

  • ½ lemon (or orange), zested and juiced
  • 1 tsp soy sauce
  • 1 tbsp balsamic vinegar
  • ¼ cup olive oil
  • Salt and pepper
  • 1 tsp honey, optional 

Steps

1. Roast the Squash:

  • Preheat the oven to 400°F.
  • Peel, halve, and deseed the squash. Cut into 1-inch cubes.
  • Place on a baking sheet, drizzle with olive oil, and season with salt and pepper. Toss to coat.
  • Roast for 20–25 minutes, flipping halfway, until golden brown.
  • Rinse and dry the seeds. Spread on another baking sheet, drizzle with oil, season with salt, and bake for 10–15 minutes until golden. Set aside to cool.

2. Prep the Kale & Veggies:

  • Remove kale ribs and thinly slice the leaves.
  • Add kale to a large bowl with 1 tsp olive oil. Massage the leaves with your hands until softened.
  • Thinly slice the fennel and apple using a mandoline or sharp knife.

3. Make the Dressing & Toppings:

  • In a small bowl, zest and juice the orange (or lemon). Add soy sauce, balsamic vinegar, olive oil, salt, and pepper. Whisk to combine. Taste and adjust seasoning (add honey if the balsamic is tangy).
  • Melt butter in a small pan. Add chopped dates and sauté for 5 minutes until caramelized.

4. Assemble the Salad:

  • Add apple, fennel, roasted squash, and dressing to the bowl of kale. Toss well to coat.
  • Transfer to a serving plate. Top with toasted seeds, caramelized dates, and shaved cheese.

Enjoy!


Other Salads to Try

Kale & Squash Winter Salad

This Kale & Squash Winter Salad combines roasted squash, caramelized dates, apple, and fennel for a vibrant, flavorful dish. Topped with a tangy homemade dressing, this customizable salad is perfect for winter meals or meal prep. Ready in under 30 minutes!
Servings: 4
Prep Time: 15 minutes
Cook Time: 30 minutes
Save This Recipe!
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Ingredients 

Salad Ingredients:

  • 1 bunch Tuscan/Dino kale, ribs removed, thinly sliced
  • 1 small squash, butternut, honeynut, or koginut, peeled, seeded, and cut into 1-inch cubes
  • 1 apple, thinly sliced
  • 1 small fennel bulb, top removed, thinly sliced
  • 5 dates, cubed
  • ¼ cup shaved manchego or parmigiano cheese
  • Olive oil
  • 1 tbsp butter
  • Salt and pepper

Dressing Ingredients:

  • ½ lemon, or orange, zested and juiced
  • 1 tsp soy sauce
  • 1 tbsp balsamic vinegar
  • ¼ cup olive oil
  • Salt and pepper
  • 1 tsp honey, optional

Instructions 

Roast the Squash:

  • Preheat the oven to 400°F.
  • Peel, halve, and deseed the squash. Cut into 1-inch cubes.
  • Place on a baking sheet, drizzle with olive oil, and season with salt and pepper. Toss to coat.
  • Roast for 20–25 minutes, flipping halfway, until golden brown.
  • Rinse and dry the seeds. Spread on another baking sheet, drizzle with oil, season with salt, and bake for 10–15 minutes until golden. Set aside to cool.

Prep the Kale & Veggies:

  • Remove kale ribs and thinly slice the leaves.
  • Add kale to a large bowl with 1 tsp olive oil. Massage the leaves with your hands until softened.
  • Thinly slice the fennel and apple using a mandoline or sharp knife.

Make the Dressing & Toppings:

  • In a small bowl, zest and juice the orange (or lemon). Add soy sauce, balsamic vinegar, olive oil, salt, and pepper. Whisk to combine. Taste and adjust seasoning (add honey if the balsamic is tangy).
  • Melt butter in a small pan. Add chopped dates and sauté for 5 minutes until caramelized.

Assemble the Salad:

  • Add apple, fennel, roasted squash, and dressing to the bowl of kale. Toss well to coat.
  • Transfer to a serving plate. Top with toasted seeds, caramelized dates, and shaved cheese.

Tried It? Let Me Know!

I’d love to see your creations! Tag me @flavorsbyalessandra on Instagram and share your thoughts in the comments below. ❤️ Buon Appetito!

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Alessandra Ciuffo

Alessandra Ciuffo is chef, creator, storyteller, and food educator. The focus of her content is on culinary education, family, travel, and lifestyle.

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