Caitlin Bensel
Active Time
20 MIN
Total Time
45 MIN
Yield
Serves : 4 (serving size: 2 pieces)

In this shoulder season, as we trade the tomatoes, eggplants, and peaches of summer for heartier fall produce, there’s one thing I get most excited about: winter squash. Sure, you can find some varieties year-round (like butternut, acorn, and spaghetti), but they are at their best—at their peak of sweetness and with the most deliciously buttery flesh—in the cooler months. Acorn squash is a favorite of mine because when it’s fresh from harvest, its skin is quite tender and delicious. I just love biting in and meeting only the tiniest bit of resistance.

And that’s why I’ve showcased this lovely squash in a preparation typically used for meat. It deserves center-of-the-plate status, after all. I’ve given it the saltimbocca treatment here, lining wedges of the squash with fresh sage leaves, wrapping them in prosciutto, and roasting to crisp up the pork and caramelize the edges of the squash. You end up with a gorgeous autumnal palette—deep orange flesh, hunter green skin, and soft green sage—and flavors that play off each other beautifully. Sage’s earthy pungency cuts the sweetness of the squash, while prosciutto adds salty notes that bring everything into balance.

But wait, that’s not all. There’s a nutty butter sauce that’s draped over the finished squash. Butter cooks in a skillet until browned and fragrant, with those toasty, caramel-like notes reminiscent of hazelnuts. A splash of dry sherry, with its raisin-y depth, intensifies the nutty effect, and a touch of citrus and honey lifts the flavors so they resonate on multiple levels, not just one.

The recipe is built to use just one average-size squash, perfect for four people. But you can easily double the recipe to serve a larger crowd. It makes such a statement at the table, you might just want to plan on that.

How to Make It

Step 1    

Preheat oven to 425°F. Cut squash in half lengthwise; scoop out and discard seeds and membranes. Cut each half into 4 wedges. Toss together squash wedges, oil, 1 teaspoon salt, and pepper in a medium bowl. Arrange wedges, cut sides down, on a rimmed baking sheet lined with parchment paper.

Step 2    

Roast in preheated oven 20 minutes, turning once halfway through. Let cool 5 minutes. Arrange 1 whole sage leaf on rounded flesh side of each squash wedge; wrap 1 prosciutto strip around each squash wedge. Arrange squash wedges on pan, skin sides down. Roast in preheated oven until prosciutto is crisp and squash is tender, 10 to 15 minutes.

Step 3    

Meanwhile, melt butter in a 12-inch skillet over medium-high, stirring often with a wooden spoon, just until milk solids begin to sink to bottom of skillet and brown, 4 to 5 minutes. Add torn sage leaves; cook, stirring constantly, just until sage stops sizzling. Remove from heat, and let stand 1 minute. Carefully stir in sherry vinegar and remaining 1/4 teaspoon salt.

Step 4    

Transfer squash to a warm serving platter, and spoon browned butter sauce over squash. Drizzle with honey, if desired. Serve immediately.

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