Roasted Brussels Sprouts Delicata Squash and Cranberries with Balsamic Syrup

Roasting Brussels sprouts and delicata squash brings out their natural sweet flavors. This easy side dish is delicious, colorful and a perfect side dish for a fall or Thanksgiving dinner.

The other day I ran into Trader Joe’s for a few quick things, and I saw something that literally stopped me dead in my tracks.  I did a double, and then a triple-take before circling the display table and then reaching out to make sure they were real.  And they were…



The most beautiful, massively huge stalks of Brussels sprouts I had ever seen, with the most perfect, small, tender sized sprouts I’d ever seen.


I know, I really need more of a life, if that’s all it takes to take my breath away.  The thing is, we don’t usually have those at the regular grocery store.  Brussels sprouts are rarely available on the stalk like that, and now that I’m describing this, it really makes me realize I need some more excitement in my life.

Brussels sprouts are one of those love ‘em or hate ‘em vegetables.  Too many people hate them because they have memories of them being boiled to death, and smelling up the house.  The trick is to roast them, so they get a little bit (or a lot) crispy and caramelized, and then they’re actually kind of sweet and crunchy/crispy.


Roasted Brussels sprouts Delicata Squash and Cranberries with Balsamic Syrup| Craving Something Healthy


Brussels sprouts are also one of the healthiest vegetables you can eat, because they fall into the cruciferous category. Other cruciferous vegetables include cabbage, broccoli, cauliflower, kale, bok choy, and arugula, and they all have lots of cancer-fighting phytochemicals.


Roasted Brussels sprouts Delicata Squash and Cranberries with Balsamic Syrup| Craving Something Healthy


I thought they would go really nicely with the delicata squash and cranberries I had on hand, and a drizzle of balsamic syrup. I was SO right.  After everything was roasted, I tossed in some fresh pomegranate arils and a handful of salty roasted pumpkin seeds.

I’m thinking this is a perfect vegetable side dish for fall and definitely for Friendsgiving or Thanksgiving. It’s got ALL the flavors and colors of the season.


Roasted Brussels sprouts Delicata Squash and Cranberries with Balsamic Syrup| Craving Something Healthy



If you haven’t tried delicata squash, please DO!  It’s sweeter and milder than butternut, and it has a nice, soft skin, so it’s easy to cut.  The skin softens so nicely when it’s roasted, that you don’t even know it’s there, so no need to trim it.


Roasted Brussels sprouts Delicata squash and cranberries with balsamic syrup |Craving Something Healthy

Roasted Brussels Sprouts, Delicata Squash and Cranberries with Balsamic Syrup | Craving Something Healthy

Roasted Brussels Sprouts, Delicata Squash, and Cranberries with Balsamic Syrup

A quick and easy side dish for fall or Thanksgiving
4.75 from 4 votes
Print Pin Rate
Course: Side Dish
Keyword: brussels sprouts, vegetables
Cook Time: 30 minutes
Total Time: 30 minutes
Servings: 6 servings
Calories: 198kcal
Author: Craving Something Healthy


  • 1 pound Brussels sprouts ends trimmed and outer leaves removed
  • 1 medium Delicata squash halved lengthwise, seeded and cut into 1-inch pieces
  • 1 1/2 cups fresh cranberries about half of a bag
  • 2 Tbs olive oil
  • Kosher salt and pepper
  • 1/2 cup balsamic vinegar
  • 1/4 cup brown sugar
  • 2 tablespoons roasted pumpkin seeds
  • 3 tablespoons fresh pomegranate arils


  • Preheat oven to 400 degrees.
  • Rinse all vegetables and cranberries well, pat dry and place in a large mixing bowl. Drizzle olive oil over all, and season liberally with salt and pepper. Toss well to coat with oil and seasoning.
  • Transfer brussels sprouts, squash and cranberries to a baking pan, so that everything is in a single layer.
  • Roast for about 30 minutes or until brussels sprouts turn brown and crisp in spots, and squash has golden brown spots. Turn vegetables halfway through roasting, to cook evenly.
  • While vegetables are roasting, mix balsamic vinegar and brown sugar in a small saucepan and bring to a boil. Reduce heat and simmer for 10-12 minutes, or until mixture thickens and turns to a syrup consistency.
  • Let vegetables and cranberries cool a bit, and drizzle with balsamic syrup.
  • If desired, sprinkle with roasted pumpkin seeds and pomegranate arils before serving.


Recipe adapted from The Pioneer Woman


Calories: 198kcal | Carbohydrates: 31g | Protein: 5g | Fat: 7g | Saturated Fat: 1g | Sodium: 42mg | Potassium: 672mg | Fiber: 5g | Sugar: 17g | Vitamin A: 1615IU | Vitamin C: 77.6mg | Calcium: 71mg | Iron: 2.2mg
Did you make this recipe?Tell me @CravingSomethingHealthy!

What’s your favorite Thanksgiving veggie side dish? Do you like Brussels sprouts?

Eat well!



  1. Kelly Anthony says:

    Such a savory side dish! Looks yummy!

    1. Craving Something Healthy says:

      Thanks Kelly 🙂

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