Warming winter salads: 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 molasses-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 bring the 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 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

Molasses-roasted squash salad with cider vinaigrette

Slightly adapted from Ina Garten aka Barefoot Contessa

For the squash

  • 1 buttercup squash, peeled and diced
  • 1-2 Tbsp. olive oil
  • 1 tablespoon Grandma 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
  • 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.

One more thing…

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Here’s to eating well, everyday,

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Roasted squash salad -squash

3 thoughts on “Warming winter salads: roasted squash salad with cider vinaigrette

  1. June Sherwood says:

    I have found a salad dressing in one of your E-Books,and can’t seem to find it now.
    I really loved it with a spinach salad with grape tomatoes, strawberries and slivered almonds. I know it had molasses in it but i think malt vinegar, or was it cider vinegar.
    Please help.
    thanks, June 🙂

  2. Gerri Hamilton says:

    How many servings are in the roasted squash salad recipe?I would like to make it for 8 and think I probably need to double it. Love your Blog!

    1. Bridget Oland says:

      Hi Gerri – To serve eight I’d double the recipe, except for the squash you could either use two small squash or one large.

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