Coat the squash in olive oil, season with salt and pepper, place on a sheet tray lined with parchment paper, and roast in the oven for 20 to 25 minutes at 375° or until lightly browned and al dente, or slightly crunchy. Transfer to a plate and chill until cold.
Next, make the pickled onions and set them aside.
Dressing: In a small bowl, whisk together the mayonnaise, sugar, red wine vinegar, olive oil, salt, and pepper, and set aside.
In a large bowl, toss together the kale, some pickled red onions, apples, fennel, celery, pistachios, and cherries, and season with salt and pepper.
Add a few tablespoons of the vinaigrette and toss together.
Finish with Parmesan cheese and top off with chilled roasted acorn squash.
Notes
Make-Ahead: You can make this spring salad up to 1 day before. Just be sure it is not yet mixed with the dressing. In addition, it would be best to leave the apples and fennel uncut.How to Store: Cover and keep it in the refrigerator undressed for up to 3 days. This will not freeze.Feel free to use whatever salad dressing you’d like.You can swap out, remove, or substitute any vegetables in this recipe.If you like more sour flavors, use granny smith apples instead of fuji or honey crisp.You can also large dice the squash instead of serving it with skin on half-moons like I did.