Roasted Squash Salad with Cider Vinaigrette

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Roasted squash salad with cider vinaigrette

Winter calls for a whole different kind of salad, salads with substance and a bit of a bite.

I think that’s why this roasted squash salad with peppery arugula and cider vinaigrette is so appealing. When the weather turns cold, “cool and crisp” are not what I crave in a salad.

Last fall we spent a long weekend in Maine with my twin brother and his wife. It was a little family getaway before the holiday rush and a chance to play tourist in an area that we often visit but never explore. On the first day we coaxed our kids through the Portland Museum of Art and puttered in the Old Port eating homemade Maine Potato Donuts, window shopping and people watching.

It was fun, sure, but we quickly decided that, why play tourist when you can hang out with your bro and his wife, cook the evenings away and try lots of new wine?

Roasted squash salad with cider vinaigrette

It was a delightfully relaxing weekend with an abundance of family time and the chance to flip through some new cookbooks.

My sister-in-law has a terrific eye for cookbooks and had just bought my brother an entire stack of Barefoot Contessa cookbooks.  An entire stack.

This roasted squash salad recipe was one of the first that I came across so I put it on the menu for one evening. I have made it six times since and I make a double batch of the dressing so I always have some in the fridge. Sometimes I top this salad with sautéed pears instead of the squash and sometimes I use both roasted squash and sautéed pears.

Roasted squash salad with cider vinaigrette

Roasted squash salad with cider vinaigrette

Slightly adapted from Ina Garten aka Barefoot Contessa

For the squash

  • 1 buttercup or butternut squash, peeled and diced
  • 1-2 Tbsp. olive oil
  • 1 tablespoon Crosby’s Fancy Molasses
  • Sea salt and freshly ground black pepper

For the cider dressing:

  • 3/4 cup apple cider or apple juice
  • 2 tablespoons cider vinegar
  • 2 tablespoons minced shallots
  • 2 teaspoons Dijon mustard
  • ¼ cup olive oil or grape seed oil
  • ½ tsp. sea salt
  • ¼ tsp pepper

For the rest of the salad

  • 5 ounces baby arugula or baby spinach, washed and spun dry
  • 1/2 cup hazelnuts, walnuts or pine nuts, toasted
  • 1/2 cup freshly shaved or grated Parmesan (omit if vegan)
  • 3 tablespoons dried cranberries or pomegranate seeds


  1. Preheat the oven to 400 degrees F.
  2. In a large bowl whisk together the olive oil and molasses. Add the cubed squash and toss to coat. Spread on a parchment lined cookie sheet in a single layer, season with salt and pepper and roast for 15 to 20 minutes, turning once, until tender. .
  3. While the squash is roasting, combine the apple cider, vinegar, and shallots in a small saucepan and bring to a boil. Boil until reduced to about 1/4 cup (precision isn’t necessary). Remove from heat and whisk in the mustard, olive oil, salt, and pepper.
  4. Place the arugula in a large salad bowl and toss with the dressing. Add the dried cranberries, nuts and parmesan. Plate each serving and top with the squash or toss the squash with the greens and serve it that way. Suit yourself.

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Roasted squash salad -squash

Roasted squash with molasses cider glaze

Servings: 6-8 serving(s)

Prep time: 10 minutes

Total time: 35 minutes

Cooking time: 25 minutes

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Drizzling roasted squash with an easy molasses cider glaze adds a lovely flavour to this winter staple. 

roasted squash with molasses cider glaze Warming winter side dishes…

If there is any consolation to shorter days and cold weather it is hearty meals made of foods that stick with you like nobody’s business.

That’s why turning the calendar to November is as good an excuse as any to cook more substantial meals and load your plate with winter vegetables and whole grains.

This isn’t about bulking up for winter, eating for the season and enjoying warming food that’s satisfying…

Of course it helps if your cold weather side dish recipes are a little healthy and get you eating your vegetables and whole grains.

Roasted squash with molasses cider glaze

Fine dining can be had at home, any night of the week.

We go through a good 50 pounds of buttercup squash each year and I have about a dozen ways that I like to prepare it.

Roasting wedges of squash is a particular favourite because it’s easy to prepare and looks pretty on a plate.

It’s especially delicious served alongside a hearty and flavourful pilaf of wild rice and hulled barley.

Pair these two dishes with roasted pork tenderloin and cranberry sauce with apple.

Roasted squash with molasses-cider glaze

  • One buttercup squash cored and cut into 8 wedges
  • Olive oil for brushing squash
  • Sea salt & fresh ground black pepper
  • 1/2 cup cider or apple juice
  • ¼ cup Crosby’s Fancy Molasses
  • 1 Tbsp. butter or olive oil
  • Salt & pepper


  1. Preheat oven to 375 F
  2. Line a large baking sheet with parchment paper and brush with oil.
  3. Lay squash wedges cut side down and brush the top side with olive oil.
  4. Season with salt & pepper
  5. Roast for about 25 minutes, flipping half way through (time will vary so keep checking)
  6. While squash wedges are roasting, combine molasses and cider in a small saucepan.
  7. Bring to a simmer , remove from heat and stir in butter (or oil).
  8. When squash are done, stand them up on their skin edge and drizzle with molasses-cider glaze.
  9. Plate and pass the leftover glaze for anyone who wants a little extra.

roasted squash with molasses cider glaze and wild rice and barley pilaf

Looking for meat to go with this recipe? Pair this dish with roasted pork tenderloin in a red currant glaze.

One more thing…

If you’re in search of family-friendly food that’s easy to prepare, healthy and tastes good, then sign up to receive blog posts by email. We’d love to send you our monthly newsletter too. It includes cooking tips, menu ideas, featured recipes and more. Here’s the link to subscribe.