Preheat the oven to 400°F and line a large sheet pan with parchment paper.
Cut the squash in half, lengthwise, stem to stem. Use a sturdy spoon to scrape and scoop out the insides and discard them. Slice each squash halve into 1-inch-thick half moons.
Add the squash rings to a large bowl, along with the olive oil, salt, and pepper. Toss to evenly coat, then turn squash out into an even layer on the sheet pan. Roast for about 30 minutes, or until nice and caramelized.
Meanwhile, combine the dried cherries, water, and vinegar in a small saucepan, over low heat. Simmer for 2-3 minutes, or until the cherries are plump. Drain and set aside.
To serve, arrange the squash on a platter. Measure out almost ¼ cup of the pesto and dollop over the squash (use more or less if you like). Then top with toasted walnuts and cherries and serve immediately.
Kale Pesto (makes 1 cup)
Add roughly chopped garlic, toasted pine nuts and finely grated parmesan cheese to the bowl of a food processor and process until smooth.
Add the kale and sage, and pulse until chopped. While the processor is running, drizzle the olive oil through the shoot until the mixture is emulsified and smooth.
Add the lemon juice, salt and pepper, and whiz again. Taste for seasoning and adjust to your liking.