In the Kitchen with Jackie — Autumn Delicata Squash Salad

Some readers are new here, so allow me to introduce myself to squash lovers everywhere! My name is Jackie and I’ve been working with Di Bruno Bros. for almost five years now — styling, photographing and sometimes cooking with all the phenomenal ingredients they offer. This little cheese-filled corner of the internet is where I’ll share the things I make. No, I am not a professional chef — I’m a home chef! I cook for my family and friends, and I’ve been known to style up a cheeseboard or two ahead of a Di Bruno’s staff meeting. As I take joy in friends and colleagues snacking on my creations, I hope this blog inspires you to cook and create, too.

Finally, it’s fall!

I won’t let the recent blast of Philly heat stop me from turning on my oven to make my favorite fall food, squash. Unlike most produce today, squash isn’t something that you can readily find year round so I like to enjoy it when I can. Right now, the markets are brimming with knobbly, brightly colored gourds, but with so many varieties to choose from, how do you decide which to take home? In my humble opinion, we should all look to the Delicata Squash

If you’re unfamiliar with Delicata, it’s small, cylindrical, and yellowish with green and orange stripes. It has quickly become my most sought after squash for a few reasons. Firstly, Delicata squash are petite and easy to prepare, unlike some other popular varieties (I’m looking at you, Butternut!). Secondly, it has a soft, edible skin, so there’s no peeling involved. Hurrah! Thirdly, they have a wonderful, sweet flavor and sure do look pretty on a plate. Are they your favorite yet? I like to use roasted squash rings in my autumn meal prep rotation. You can start out eating them as a side, then they can go on a salad, and if there’s any leftover near the end of the week they can be blended into a soup. So many possibilities!

I knew that I wanted to make a salad for this post featuring my beloved Delicata, so I consulted our cheesemonger, Davey Jeff, at the Franklin. He talked me through a few options: A fresh goat cheese would be too obvious, but have I thought about shaving a firm cheese? How about a gouda, such as Brabander or L’Amuse? What kind of dressing would you put on it? He asked questions not unlike a doctor deducing the best remedy for a patient. After a few trips around the cheese counter, we landed on shaved Parmigiano Reggiano, because I knew I wanted to use our Fig & Acacia Honey Jam for a figgy dressing (and Parm and figs are old friends).

“He asked questions not unlike a doctor deducing the best remedy for a patient.”

Now this salad is starting to take shape! We’ve got a base of spicy arugula, roasted squash rings, shaved Parm, and a figgy balsamic dressing. We’re still in need of some crunch. For me, the key to making salads interesting is texture variety. If it’s all one note, count me out! Pistachios felt like a good choice because they jive well with Parm and fig flavors. 


We just need one more thing. Prosciutto! But instead of soft slices, I wanted even more crunch so I decided to bake the prosciutto into chips that will crumble into salty little pieces. If you’re concerned that it’s a waste of perfectly good prosciutto, I promise you’ll thank me later.

Once you’ve made the salad, you’re left with the components of a delightful autumn cheese board. Arrange squash rings with Parm and pistachios. Drizzle with the fig molasses or balsamic, go nuts! Make more fig dressing and try it on chicken or pork.

Autumn Delicata Squash Salad with Figgy Dressing
Makes roughly 4 salads

2 Delicata squash, seeded and cut into half inch rings
La Quercia Prosciutto 
1 TBSP DB Classico Olive OIl 
Fine Sea Salt
Cracked black pepper
Parmigiano Reggiano, shaved
¼ CUP pistachios , shelled and roughly chopped
5 OZ bag of arugula
½ CUP DB Sicilian Extra-Virgin Olive Oil
3 TBSP DB “Silver” Barrel-Aged Balsamic Vinegar
½  TBSP DB Fig & Acacia Honey Jam
½  TBSP Fig Molasses
¼ TSP fine sea salt, to taste
A garlic clove finely minced 

Roast the squash and bake the prosciutto

  1. Preheat the oven to 425°F. 
  2. Cut both ends off the squash. Cut it crosswise through the middle. Scoop out the seeds from each half. (I like using a serrated grapefruit spoon for my squash scooping).
  3. Now slice the two halves into ½ inch rings.
  4. Toss the rings in a bowl with 1 TBSP of olive oil, 1/4 TSP of kosher salt and a few grinds of cracked black pepper.
  5. Arrange the rings on a parchment lined baking sheet and roast in the preheated oven for 22 minutes total, flipping halfway through. 
  6. Assemble slices of prosciutto on a parchment lined baking sheet as well and put in the oven along with the squash. Bake for 12 minutes. When they are stiff and crispy remove them from the oven.
  7. At this time flip the squash and bake for about 10 more minutes. The squash should look lightly browned and tender.

Make the Dressing

  1. In a bowl or jar combine olive oil, vinegar, jam, garlic and molasses. Vigorously whisk together to create an emulsified vinaigrette. (I like to make it in a mason jar and shake it up so I can put a lid on it and use it later.) Add salt and black pepper to taste.

Assemble the salad

  1. Start with a base of a few handfuls of arugula.
  2. Layer a few rings of squash.
  3. Shave the Parm over top using a vegetable peeler or mandoline on a thin setting.
  4. Drizzle the figgy dressing.
  5. Sprinkle with pistachios and crumbled prosciutto chips.


Previously on In the Kitchen with Jackie:

Cacio e Pepe