Winter Squash Salad with Dried Fruit and Port Dressing

Gathering with friends and family for meals brings much needed light into the dark days of winter. On those occasions, I love having a new dish to share that has a bit of sparkle in it. This winter salad brings roasted butternut squash, leafy greens, toasted nuts, dried cherries and cranberries together in a colorful mix. It’s lightly dressed in vinaigrette that features Port. And then topped with warm discs of baked goat cheese. Sparkle? Brightly!

I adapted this recipe from one I found in the RSVP section of the November 1999 issue of Bon Appétit. A reader from Germany had written in, requesting the recipe for “the most exquisite salad ever” that she had eaten  at 300 East Boulevard (now called 300 East) in Charlotte, North Carolina. Almost twenty years later, the restaurant still offers a version of this starter.

The Port Dressing

The dressing for this salad—which uses Port, a wine usually meant for after-dinner sipping—is very special. The original recipe called for dried tart cherries, but because my pantry was low on those, I combined the few I had with some dried cranberries. They soaked in the warm Port, swelling up with flavor and glistening like garnets.

The original salad featured crisp pancetta and its drippings to build the Port dressing, but I opted to highlight vegetables instead. I began by sautéing finely chopped shallots until they were soft and sweet. Next, minced garlic, vegetable oil, red wine vinegar, and a bit of sugar built the next layer of flavor. Finally, the steeped cherries and cranberries along with the Port went in. Blended with the shallot mixture, they completed the salad dressing.

The Salad

To provide a further dimension, I turned to roasted butternut squash. The lovely orange color and slightly caramelized flavor of roasted winter squash complement the other salad components beautifully.

While this salad has ingredients that make it special, most can be prepared well ahead of time to make assembly pretty quick. The final touch, crowning the fresh salad with warm slices of goat cheese, does happen at the end. And it is worth it.

I used floss to slice the goat cheese into equal-sized discs and then placed them on a foil-lined sheet pan to bake.  And after a couple of attempts, I learned to allow the rounds to cool for a bit after baking before transferring them to the salad.  This method created warm ovals of creamy, tangy cheese that kept their shape.

Once assembled, this winter salad offers fresh green leaves adorned with golden cubes of roasted squash and bright-tasting, plump dried fruit. The crunch of the pine nuts alongside the velvety goat cheese completes the flavors.  

It is a salad “most exquisite” and  worthy of a celebration.

Winter Squash Salad with Dried Fruit and Port Dressing

Sunnyside Cook

Dawn Dobie

A celebration salad combining greens, roasted squash, and pine nuts with a dried fruit and Port dressing.

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Prep Time 20 minutes mins

Cook Time 25 minutes mins

Total Time 45 minutes mins

Servings 4

Ingredients

  

For the dressing:

• 1/4 cup dried tart cherries
• 1/4 cup dried cranberries --unsweetened, if possible
• 1/2 cup tawny Port
• 2 tablespoons olive oil
• 3-4 shallots finely chopped
• 1 garlic clove minced
• 3 tablespoons vegetable oil --such as grapeseed or canola
• 3 tablespoons red wine vinegar
• 2 teaspoons sugar
• Salt and freshly ground black pepper

For the salad:

• 1 tablespoon olive oil
• 1/2 butternut squash peeled, seeded, and cut into 1-inch cubes
• 1 5- ounce bag fresh spinach leaves or mixed salad greens
• 1/2 cup pine nuts toasted
• 1 5.5- ounce log soft fresh goat cheese cut into 1/2-inch slices (I used floss to slice them)

Instructions

 

For the dressing:

• Combine the dried cherries and cranberries in a bowl. Place the Port in a glass measuring cup and heat in the microwave on High for 1 minute. Add the dried fruit to the Port and allow to sit for at least 15 minutes. (Or heat the Port in a small saucepan over medium heat until it reaches a simmer and add the fruit. Remove from the heat and allow to sit for 15 minutes.)
• Heat the 2 tablespoons of olive oil in a small skillet over medium-low heat and add the chopped shallots. Cook slowly for about 5 minutes, until the shallots are softened and golden. Add the garlic and cook an additional minute. Add the vegetable oil, sugar, and red wine vinegar, stirring to help the sugar dissolve. Remove from the heat and add the Port and dried fruit mixture. Add salt and black pepper to taste. Set aside.

For the salad:

• Preheat oven to 425 F.  In a large bowl, toss butternut squash cubes with 1 tablespoon of olive oil and season with salt and freshly ground black pepper.  Transfer to baking sheet (I lined mine with foil) and bake for 15 minutes, stirring halfway through.  Remove from oven and allow to cool to room temperature.
• Reduce oven heat to 350 degrees F. Place goat cheese slices on baking sheet lined with foil or parchment paper. Bake for about 7-8 minutes, until warmed through. Remove from oven and place on rack. Allow to cool 5 minutes.
• Meanwhile, toss the spinach (or greens) with the squash and pine nuts in a large bowl. Rewarm the salad dressing over medium heat and pour a bit over the salad. Toss to blend, adding more dressing if needed. Top with rounds of warm goat cheese and serve.

Notes

The salad dressing can be made 2 days ahead of time.  Transfer to a container, cover, and refrigerate.  Rewarm before using.

The squash can be roasted up to 2 days ahead of time. Transfer to a container, cover, and refrigerate.  Bring to room temperature before assembling the salad.

If you are toasting the pine nuts yourself, start them in a dry skillet and cook over medium heat until they are golden brown.  Transfer to a dish and allow to cool.  They can be toasted up to 5 days ahead of time.  Cover and refrigerate, then bring to room temperature before using.