This is an Italian approach to cooking winter squash; thin cut and pan seared, finished with rosemary and white wine. The result can be a sweet taste of the squash, so I top it with arugula and pepper infused olive oil. The result is a lovely contrast of flavors and texture.
My preferred squash for this Winter Squash with Rosemary is a Candy Roaster — a unique heritage plant from the Cherokee nation commonly available around the Carolinas and North Georgia. This interesting squash is very sweet with a unique flavor perfect for this dish. However, butternut, Hubbard, acorn, pumpkin and other thick flesh squashes also work.

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Cooking winter squash on the stove top is a bit unusual. Cutting the squash into thin slices is required to make it work. How thin you might ask? Frankly, it depends on how hard the squash is. If the squash is soft, thin slices will fall apart. Harder squashes can be thinner. Shooting for 1/4 inch is a good starting point.
Notes on Technique
The sauté step in this recipe is a bit different. The squash is sautéed in olive oil to produce caramelization; a standard technique, but not usually applied to squash. Also, the garlic is added to the initial sauté then removed. This gives a hint of garlic — a very standard Italian technique.
Notes on Ingredients
Squash
As discussed many types of winter squash work well with this recipe. In addition to the preferred candy roasters, butternut and Hubbard work well, as do others. You need to consider two factors. The skin needs to peel off easily and because you are pan searing it, the flesh needs to be somewhat thick so as to not fall apart.

Pepper Oil
To provide a finishing touch, we will add some pepper infused olive oil. Your choice as to what peppers you would like to use, but I suggest medium hot dried peppers for a couple of reasons. Medium hot provides the contrast without overcoming the squash taste and a dried peppers last longer if you want to keep the infused olive oil for another reason.
Infusing olive oil is pretty easy. Have a very clean container ready, warm the oil and mix in the herbs. Straining or not is your choice. But prepare the oil well ahead to make life easier for yourself. Please see my full discussion on Chili Infused Olive Oil.
Arugula
Arugala is the right taste for this. The bite it adds is perfect.
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Winter Squash with Rosemary
An Italian Twist to a winter staple
Ingredients
Pepper Infused Olive Oil
- 1 cup olive oil
- 3-4 dried peppers
Sautéed Squash
- 1 ½ pounds Winter Squash (use butternut, acorn, candy roaster or similar)
- 2 - 3 tablespoons olive oil (enough to just coat bottom of the pan)
- 2 garlic cloves
- ½ cup white wine
- 1-2 tablespoons finely chopped fresh rosemary
- Salt and Pepper
Arugula and Olive Oil Dressing (Topping)
- 1 bunch arugula
- Pepper infused olive oil (to taste)
Instructions
Pepper Infused Olive Oil
The infused oliive oil needs to be made in advance. Depending on whether you use fresh pepper or dried pepper a few hours or days in advance. (See notes)
- Sterilize the storage bottle by washing a glass bottle or jar in hot, soapy water, rinse well, and let dry.
- Add the pepper flakes to the olive oil. Gently warm the olive oil on low heat to 140°F (60°C).
- Cool the oil and store in a cool, dark place or in the fridge. Since dried pepper flakes are used, the oil can be stored for up to a month..
Sautéed Squash
- Peel the squash. Slice thin (less than a ¼ inch or 5 mm thick).
- Smash the garlic cloves with a side of a knife.
- Heat the olive oil in a wide flat pan. Add the garlic and squash and cook over medium heat, stirring occasionally with a spatula careful to not break up the slices.
- Cook until the garlic starts to brown and the squash lightly sears. Remove the garlic and discard it.
- Add the wine and cook until it mostly evaporats..
- When the liquid is almost fully reduced, lower the temperature and simmer lightly until the squash is tender. As it finishes, add the rosemary and cook for a bit longer.
- Serve while warm, topped with arugula drizzled with the pepper infused olive oil.




