Pasta alla Vodka with Roasted Winter Squash

3-4 lbs. winter squash, such as butternut or kabocha (peeled if using butternut), seeded, and cut into 3/4-inch pieces (about 4-1/2 c.)
4 T. olive oil, divided
1 t. granulated sugar
3 t. kosher or sea salt, divided, plus 1 T. for pasta water
Freshly ground black pepper
1 small red onion, diced
3 medium-sized garlic cloves, minced
1/4 - 3/4 t. crushed red pepper flakes [or less, for less spice]
1 28-oz. can whole tomatoes, coarsely chopped, juices reserved
1/2 c. vodka
2/3 c. heavy cream
1 lb. dried pasta [bowtie or penne recommended]
1 c. finely grated Parmigiano-Reggiano cheese, plus extra for garnish
1/3 c. chopped fresh basil

Heat oven to 450 degrees. Toss squash with 2 T. olive oil, sugar, 2 t. salt, and a generous grind of pepper. Roast until tender and browned on the edges, 25-30 minutes, stirring once partway through cooking. Meanwhile, bring a large pot of water to a boil over high heat. Add 1 T. salt to the water for cooking.

While squash is roasting, heat the remaining 2 T. olive oil in a large saute pan or skillet over medium heat. Add onion and cook, stirring occasionally, until softened and starting to brown, about 6 minutes. Add garlic and red pepper, stirring to combine, and cool until garlic is fragrant, about 1 minute. Stir in tomatoes with juices, vodka and 1 t. salt; cook and additional 10 minutes, stirring occasionally, lowering heat if sauce starts bubbling too vigorously. (You want a gentle simmer.) Stir in cream, cook and additional minute, and set aside.

While sauce is simmering, turn water to high heat and cook pasta according to package directions, until just al dente. Reserve 1/4 c. cooking water and set aside.

Drain pasta, return it to the pot over medium-high heat, and toss with squash and reserved pasta water. Stir in tomato-vodka sauce and cheese until thoroughly combined. Cook until sauce is thickened and pasta is nicely coated, about 3 minutes. Remove from heat, toss with basil, sprinkle with extra cheese, and serve.

Serves 6.

From Yankee magazine, Sept./Oct. 2012, p. 66.