A fall and wintertime salad worth keeping around, this Arugula and Winter Squash Salad gets a unique twist thanks to a citrusy-sweet Vanilla Orange Vinaigrette!
I'm always looking for fun ways to keep greens in my diet throughout the cold seasons, and like a Warm Winter Kale Salad with Maple Vinaigrette this hearty salad does the trick. Arugula not your thing? Swap it for kale to keep similar vibes!

Quick look at the recipe
Ready In: 35 minutes
Servings: 6
Nutrition: 281 calories
Main Ingredients: Buttercup squash, arugula, fresh orange juice, vanilla bean
Dietary Notes: Gluten free, Grain free, Dairy free
Why You'll Love It: Interesting flavor and textures. Easy to make it a meal!
Have a Question? Want a Summary?
Ask AI to summarize or ask a question about this salad recipe!
Disclosure: these buttons are meant to be helpful but I am not responsible for how AI answers.
Hearty salads keep mealtime interesting while delivering a massive amount of nutrition and fiber. Peppery arugula holds up well with grains or squash, as I found out with this Wild Rice & Arugula Salad with Maple Tahini Vinaigrette.
The vanilla-orange vinaigrette lends a unique flavor to this wintertime salad, originally inspired by a recipe in Midwest Living magazine!
While this isn't a high protein meal on its own, you simply need to pair with protein for a complete meal, like this Wild Rice Salad with Chicken & Kale which also sports an orange dressing! That said, salmon or steak would go great with this salad, too.
Jump to:
Electrifying vanilla orange vinaigrette

It's no secret that this vanilla orange vinaigrette is what makes this squash salad unique. After all, when's the last time you considered putting vanilla bean in your salad?
If you can, use a vanilla bean or vanilla bean paste for this recipe. You'll see the vanilla bean in the dressing and in the salad itself - almost like poppy seeds!
That said, you can substitute pure vanilla extract if needed. Use 1 teaspooon for this recipe.
Beyond that, fresh orange juice adds brightness to the dressing, similar to my meal prep favorite Wild Rice Salad with Chicken & Kale. The hardest step is to reduce the orange juice a bit on the stovetop so the dressing isn't too watery.
Which type of squash works best

Winter squashes are the star of this salad, but which one should you use?
I used a blend of buttercup and kabocha squash for this recipe. Honestly, any dense, hardy squash should work!
I'm pretty vocal about thinking butternut squash is bottom tier. So while it's on the list, I encourage you to try something new with this salad recipe - I bet you'll love buttercup squash!
Squashes to use for this recipe (feel free to mix and match!):
- Buttercup
- Turban
- Kabocha - use leftovers for Kabocha Squash and Apple Soup
- Butternut
- Candy Roaster
Top Tips from Chelsea
Vanilla bean is worth the splurge. This dressing is pretty unique, both via flavor and appearance, since you can see those specks of vanilla bean in the salad. Because of that, it's worth buying vanilla beans or vanilla bean paste just for this recipe!
Mix and match squashes for a unique flavor! Feeling frisky? Grab a couple varieties of squash and mix and match for the recipe, using about 2 cups of each.

Repurpose the vanilla bean pod
Once you've scraped the pulp and seeds out of the vanilla bean, don't throw out the pod! Here are a couple ways to use it:
- Add to a jar with sugar and keep sealed for a week or two for vanilla sugar.
- Add to a custard like Dairy Free Banana Custard while on the stovetop and remove before pouring into ramekins.
- Simmer while making a Ginger Masala Chai Latte for vanilla flavor.
FAQs
Use whatever hardy, thin-skinned squash with rich, dense flesh you can get your hands on! I like buttercup or kabocha for this recipe, but turban squash and butternut also work well.
If arugula isn't your jam, feel free to substitute kale or spinach.
Yes, feel free! You'll need about 1 teaspoon vanilla bean paste.
All the squashes I've recommended have edible skin; it's up to you whether you want to deal with peeling it or not!

More salad recipes with squash
Love these hearty squash salads? I've got several on Chelsea Joy Eats, because I love them too!
- Roasted Grape Salad with Delicata Squash
- Warm Winter Kale Salad with Maple Vinaigrette
- Roasted Beet & Butternut Squash Salad with Wild Rice
- Warm Kale & Butternut Squash Salad with Cranberries & Walnuts
On the other hand, if you're eyeing gluten free salads without squash, here are some favorites:
Did you try this Arugula and Winter Squash Salad recipe? Please leave a comment and rating or tag me on Instagram - I love your feedback.
Print📖 Recipe
Roasted Winter Squash & Arugula Salad with Vanilla-Orange Vinaigrette
- Prep Time: 15 minutes
- Cook Time: 20 minutes
- Total Time: 35 minutes
- Yield: 6 servings 1x
- Category: Salad
- Method: Roasted
- Cuisine: American
- Diet: Dairy-Free, Gluten Free, Vegetarian
Description
This unique fall or winter salad brings arugula and winter squash together with a unique vanilla orange vinaigrette. Feel free to swap in a different dense winter squash or mix-and-match a couple varieties for a different vibe!
Ingredients
- 4 cups chopped buttercup squash
- ¼ cup plus 1 tablespoon olive oil, divided
- 1 teaspoon salt, divided
- ½ teaspoon freshly ground black pepper
- ⅔ cup fresh orange juice (from about 3 oranges)
- 1 vanilla bean pod
- 1 tablespoon white wine vinegar
- 2 teaspoons honey
- 1 tablespoon chopped shallot
- 5 ounces fresh arugula (about 3 cups loosely packed)
- ½ cup dried cherries or cranberries
- ½ cup toasted walnuts (see NOTES)
- 2 ounces feta cheese or goat cheese, crumbled (omit for dairy free)
Instructions
- Roast the squash. Preheat the oven to 450 degrees F and line a rimmed baking sheet with parchment paper. Add the squash to the baking sheet and drizzle with 1 tablespoon olive oil. Season with ½ teaspoon salt and pepper, tossing to coat. Spread evenly on the baking sheet and roast for about 20 minutes, until tender. Remove from oven and let cool.
- Prepare dressing. In a small saucepan, bring the orange juice to a boil over medium-high heat. Reduce heat and simmer uncovered for 5-10 minutes, until reduced by about half. Meanwhile, carefully slice the vanilla bean lengthwise to open it up. Using the back of the knife, scrape the seeds and pulp out of the vanilla bean.
- Add the orange juice, vanilla bean seeds/pulp, white wine vinegar, honey, shallot, and remaining ½ teaspoon salt to a blender and blend on high speed. While the blender is running, slowly drizzle in the remaining ¼ cup olive oil through the opening in the lid until emulsified. The dressing should look light and creamy with tiny vanilla bean seeds visible.
- Assemble salad. Add arugula and cooled squash to a large bowl and drizzle with about half of the dressing and toss to coat. Arrange on a platter if desired or keep in the bowl. Top with dried cherries or cranberries, toasted walnuts, and feta cheese. Drizzle with remaining dressing or serve alongside.
Notes
FOR TOASTED WALNUTS: To toast the walnuts, either scatter over the squash during the last 5-7 minutes in the oven OR add to a dry skillet set over medium-high heat for 3-5 minutes, stirring frequently, until fragrant.
REUSE VANILLA BEAN POD: Once you've scraped out the seeds and pulp from the vanilla bean pod, don't throw it out! You can add the pod to a jar with sugar to make vanilla sugar, or add to the pot while making custard for vanilla flavor.

Leave a Reply