This salad makes a nice side to lamb chops and a glass of Merlot.
Preheat the oven to 420 F. Position the racks on the upper and lower third of the oven. Line two baking sheets with parchment paper.
Roast the butternut squash: On one of the baking sheets, toss the butternut squash cubes with extra virgin olive oil and season with salt and pepper. Place on the lower third oven rack. Roast for 20 minutes and then toss and continue to roast for another 15 minutes.
Croutons: On the other baking sheet combine bread cubes with pumpkin seeds. Toss and coat the bread and seeds with extra virgin olive oil. Arrange in a single layer. Roast for 10-13 minutes on the upper third rack in the oven.
Vinaigrette: In a small bowl add all the vinaigrette ingredients except the olive oil. Whisk together to mix. Slowly add the olive oil whisking to emulsify the vinaigrette.
Kale: In a large bowl add the chopped kale and about 1/4 of the vinaigrette. Mix well to coat the leaves. With clean hands massage the kale leaves for about 30 seconds.
To serve: Add the dried cherries and shallot slices to the bowl of kale, mix. Drizzle a little vinaigrette and mix again. Add the roasted butternut squash and crouton mix, gently toss and mix. Drizzle in the remaining vinaigrette and toss.