Preheat your oven to 400° F. Spread diced butternut squash on a foil-lined sheet pan, drizzle with olive oil, and season with salt and pepper. Roast for about 20 minutes until fork-tender.
In a small bowl or jar, whisk together balsamic vinegar, dijon mustard, maple syrup, and olive oil. Adjust to taste and set aside.
While the squash is roasting, prep the other ingredients: quarter the hard-boiled eggs, chop the bacon, and dice the apple.
Start with a base of mixed greens or lettuce in a large serving bowl or platter.
Layer the roasted butternut squash, diced apple, chopped bacon, quartered eggs, crumbled goat cheese, dried cranberries, and pepitas over the greens.
Drizzle the vinaigrette over the salad or serve on the side for individual dressing.
Serve the salad and enjoy the blend of flavors.