Squash Sensations: A Winter Squash Primer

By: Naomi Ross

Visiting a farm or produce market this time of year is a seasonal treat for squash lovers among us. Autumn vibes go hand in hand with seeing overflowing displays of every type of pumpkin, squash, and gourd. Mimicking the changing greens, oranges, and yellows of fall foliage, the array of varietals abounds with more types than we recognize or even know how to cook!

Though butternut and acorn squash happen to be the most commonly found supermarket varieties available, there are many others worth trying—sweet dumpling, banana, delicata, spaghetti, kabocha, and buttercup varieties, just to name a few. Each type has its own special flavor and texture appropriate for different uses. Some have sweeter, creamier flesh for purees, while others are perfectly shaped and suited for stuffing purposes.

Squash Tips:

Due to its thick peel and hard texture, winter squash can be tough to prepare, but don’t be discouraged—a good peeler, a sharp chef’s knife, and some “elbow grease” can make all the difference in your preparations. Even so, some prep tips are always helpful.

• For winter squash with a thin or smooth enough rind to be peeled, (such as butternut or buttercup squash), follow these steps for an easier prep:

1. Trim ends

2. Cut the squash in half lengthwise

3. Using a good peeler, peel away the tough skin until reaching uniform yellow colored flesh

4. Scoop out the seeds

5. Cut as needed (i.e., chunks, cubes, dice)

Once peeled and cut, it can be boiled, roasted, steamed, sautéed, etc. and used in your favorite dishes.

• Round acorn, sweet dumpling, and delicata squash are not practical to peel as the natural grooves make peeling hard to maneuver. Most people opt to cook them unpeeled—simply scrub, halve, seed, and bake. The skin is edible. However, if tough, the cooked flesh can be scooped and eaten out of its “cup,” discarding the skin. I like to roast the halves drizzled with maple syrup, olive oil, salt, pepper, and cinnamon—simple, yet delicious! Additionally, these small-sized squash make them ideal choices as “stuffing” squash.
• Squash puree is essential for baking. The most conventional method is to use boiled/steamed cubed squash. That said, the easiest method of preparation is pre-roasting: cut squash in half, scoop out the seeds, and bake cut-side down at 375–400F° until fork tender (about 45 minutes). Once baked, the cooked flesh can be scooped out of the skin and then mashed or pureed.
• Winter squash store very well. They’ll last the “winter” in a cool, dry, well-ventilated location (like a cellar) for use within 2 – 4 months. Check periodically for rot.
• Refrigerated, cut pieces of winter squash will last up to a week stored in plastic storage bags or wrap.
• Choose firm, well-shaped squash that are heavy for their size and have a hard, smooth skin. Avoid any with sunken or moldy spots, cuts, or punctures in the skin.
• Some helpful equivalents in your squash adventures may include:
  • 1 pound peeled squash = 1 cup cooked, mashed
  • 2 1/2 pound whole squash = 2¾ –3 cups pureed
  • 1/3–1/2 pound raw unpeeled squash = 1 serving
• Serving cute mini squashes is an easy and fun fall presentation. When purchasing, figure half a mini per person.

Mini squash are perfect for individual portions and for stuffing. Any mini winter squash can be used with this simple method, but I do favor baby sweet dumplings. While I like to serve these freshly made, the squash prep is very easy to do 1–2 days ahead, and then it is 5 minutes to assemble and get into the oven!

Serves 8

Cook’s Note: The larger or thicker the squash, the longer the cook time.

Ingredients:

4 mini winter squash (e.g. sweet dumpling, baby acorn, gold nugget, etc.)

Kosher salt, to taste

Freshly ground black pepper

1/2–3/4 teaspoon cinnamon

1/4 cup pure maple syrup

1/4 cup olive oil

1 cup fresh cranberries

Directions:

1. Preheat oven to 375°F. Line two baking sheets with foil or parchment paper.

2. Cut squash in half, scoop out seeds and any fibrous strings. Trim bottoms if needed so the squash halves sit flat on the baking sheet. Place squash halves on lined baking sheets.

3. Sprinkle each half with salt, pepper, and cinnamon. Drizzle maple syrup and oil over halves, brushing the liquid to coat the whole cut area. Fill each half with approximately 8–10 cranberries (or as many as fit comfortably). Roast for 25–35 minutes, or until squash is tender when pierced with a fork and cranberries are bubbling. 

Naomi Ross is a cooking instructor and food writer based in Woodmere, NY. She teaches classes throughout the country and writes articles connecting good cooking and Jewish inspiration. Her first cookbook, The Giving Table, was released in 2023. Follow her @naomirosscooks on Instagram/FB or visit her website: NaomiRossCooks.com.