Tomato and Kale Stuffed Delicata Squash

September 01, 2020

Recipe by Local Roots recipe contributor, Chef Casey Corn @casey_corn

I’m so thrilled to be back doing Local Roots recipes, that I used my whole share to make this recipe! I had some leftover filling, so I made some orzo and tossed it in the sauce and then added a fried egg for brunch the next day!

Tomato and Kale Stuffed Delicata Squash


for the tomato sauce:

3 ea (1.25 lb) heirloom tomatoes

2 Tbs extra virgin olive oil

1 tsp kosher salt

½ tsp ground pepper

1 ea bay leaf


½ ea large yellow onion

5 ea garlic cloves

1 Tbs extra virgin olive oil

1 bu purple kale

1 tsp kosher salt

1 ea rosemary sprig

5 ea thyme sprigs

⅓ c goat cheese


for the squash:

2 ea large delicata squash

2 Tbs extra virgin olive oil

1 Tbs kosher salt



Start by making your tomato sauce. Core the tomatoes and roughly dice them, reserving the liquid. Transfer tomatoes with all liquid into a medium pot with the bay leaf, olive oil, salt andground pepper. Bring up to a simmer, then cover and lower heat. Simmer the tomato sauce for about 20-30 minutes, until skins are soft. Discard the bay leaf. At this point, you can use a hand blender to puree, or leave it chunky. Keep warm.

Preheat the oven to 400F.

While your sauce is simmering, prep the rest of your vegetables. Finely mince the onion and garlic cloves, and finely shred the kale, discarding the stems. Cut the ends off of the squash, and cut in half, creating two squash tubes. Scoop out the seeds. Brush with the olive oil on the inside and outside, and season with salt.

Prepare a baking sheet by lining with foil. Cut a small square of foil for each of your squash tubes: you’ll be wrapping the bottom of each to keep the filling in while they cook. Place each squash tube on a square, and wrap it around as tightly as possible. Put the squash on the baking sheet standing up, with the foil on the bottom, and then place in the center of the oven. Roast for about 20 minutes, then remove and allow to cool while you finish preparing the filling.

In a large skillet, warm a tablespoon of olive oil and saute the onion until soft and translucent, about 5 minutes. Add in the garlic, and let soften, about 2 minutes. Raise the heat up to medium high, and stir in about half the kale, trying not to overcrowd the pan. When the kale has wilted, add in the rest, and toss to prevent the onion and garlic from clumping.

Season the kale with salt, then lower the heat and add in the herbs and the tomato sauce. Stir to combine, and let the sauce slowly simmer for about 10 minutes to bring all the flavors together. Stir in the goat cheese.

Spoon the filling into the squash tubes, all the way up to the top. Place back in the oven for about 20-25 minutes, until the squash is fork-tender.

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