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If roasting pears is new to you, you’re in for a treat. Before adding these to the squash filling, be sure to sneak a couple for a taste test. They’re like candy!

A delicious twist on basic spaghetti: Baking it with spinach, sausage and cheese melds the flavors deliciously and creates a one-dish meal that’s almost as good as lasagna—without all the work. Use a smaller or larger amount of meat, as desired, or omit completely for a vegetarian version.

Serves: 4

Ingredient Notes

1. Squash Dumpling and delicata squash are recommended since they are more consistently sweet and flavorful. If the dumpling doesn’t have a very big stuffing cavity, scoop out a little of the pulp prior to stuffing. The extra pulp can be combined with a little pear stuffing in a small, oiled baking dish, casserole style.

The more common acorn squash can be substituted (either 2 medium-sized or one large), but they are sometimes fairly bland and grainy tasting. So taste before stuffing to make sure you have a good foundation; the finished dish will only be as good as the squash you start with. This brings up the whole point of squash quality.

Although dumpling and delicata squash are generally more dependable, all squash carry the potential for being flavor-less, and often there’s no exterior indication of this deficiency, you discover it only after baking and tasting the squash!
The only semi-reliable indicators I know are age and weight, i.e., if a squash is old and very light-feeling for its size, this often indicates a squash that is dried out and low on flavor.
It helps to have a good source. There are a couple farmers in our area whose squash have a high success rate, so I try to buy from those farmers. Smaller, organic farms seem to have a better success rate in general, although participants in my cooking classes have gotten good squash at the regular grocery store.
Another good indication of a dud squash is one that doesn’t soften up nicely as it cooks but stays dry and hard. If a squash is going nowhere after an hour of baking, it is probably going to be tasteless.
My strategy: It never hurts to have some extra cooked winter squash in the frig–it can easily morph into a great winter meal. So whenever I turn the oven on to bake squash, I maximize my energy usage and cook several–often different kinds. Then I have a backups in case one squash turns out to be a dud. This is particularly important if you’re having guests for dinner!
As mentioned above, tasting is the only way to gauge a squash’s quality for sure. I have been surprised several times by a squash that didn’t look promising but turned out just fine.

2. Sherry Wine The sherry is a key flavor in this dish. Be sure to use an actual sherry wine from a liquor store, rather than the salty cooking sherry found in grocery stores. A true wine doesn’t cost any more, but it tastes much better. Cribari and Taylor are two common, reasonably priced and perfectly adequate labels.

An elegant-looking dish that is perfect for company or holiday meals–but not so time-consuming it can’t be made for a regular weekend meal. Be sure to double; it makes great leftovers for the work week.
Ingredients	Instructions
2 med. to large dumpling or delicata winter squash, halved and seeded 4 tsp. olive oil Sea salt and freshly ground pepper, to taste	Roast Squash Preheat oven to 400 (F). Cut squash in half, scoop out seeds and place, cut side up, on a cookie sheet. Drizzle about 1 tsp. olive oil over each squash half and, using your hand, rub it over entire cut surface of squash. Sprinkle with salt and pepper. Place squash in oven and bake until quite tender when stuck with a fork, which will range from 20 to 60 minutes, depending upon the size and type of squash. It is normal (and tasty) for squash to brown slightly.
4 to 5 med. Asian pears or 3 to 4 Bosc pears, cored and diced to about ½” (about 4 cups) ½ Tbsp. butter	Roast Pears Combine pears and butter in an 8 x 8” baking dish and place in oven. Once butter melts (in about 10 minutes) stir to coat pear pieces evenly. Return pan to oven with squash and roast until pears are lightly browned on the outside, about 30 to 40 minutes. Stir and flip pears halfway through the cooking time.
2 large leeks, white and light green parts, diced to about 3/4” (about 4 cups)	Steam Leeks While squash and pears roast, steam leeks for 5-7 minutes, just until tender and no longer sharp tasting. Leeks should still be brightly colored. Remove promptly from steaming pan and set aside.
¼ tsp. ground nutmeg ½ cup sherry wine + 2 more Tbsp. Sea salt and freshly ground pepper, to taste	Assemble Stuffing When pears are done cooking, sprinkle with nutmeg, drizzle with ½ cup sherry, then stir to loosen pears and scrape up any butter and pear bits on bottom of pan. Add reserved leeks and stir to combine thoroughly. Taste and season with salt and/or pepper, to taste. Stuff Squash and Bake Briefly When squash are finished roasting, remove from oven. (Optional step: prick cavities all over with a fork. Pour the 2 Tbsp. sherry equally over squash halves and mix lightly with a fork so sherry penetrates squash evenly.) Pile equal portions of pear-leek mixture into each squash half. Cover pan loosely with recycled or reused foil and bake another 20 more minutes to warm everything and meld flavors. Serve immediately.

Stuffed squash makes a lovely presentation. Pictured here are a stuffed dumpling (on the left) and a stuffed acorn (on the right.)

Roasted Pears

Bosc Pears

Both Bosc and Asian pears will work well in this dish. While Asian pears have a unique flavor that is nice with the sherry, it’s more important to use a pear that is flavorful, which can only be determined by buying both and tasting. Don’t worry, any extra pears have dozens of uses, or just eat them as is!

Winter Squash with Sherried Pear Filling

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