Trim the ends off each squash and cut in half lengthwise. Scrape out the seeds and any stringy bits with a spoon and discard. Cut the squash into ½-inch thick slices.
Toss the squash with the olive oil, salt, and pepper in a large mixing bowl or directly on a large parchment-lined rimmed baking sheet. Spread out into a single layer on the baking sheet.
Roast for 15 minutes or until lightly browned on the bottom. Flip slices over and continue roasting until browned on the other side and tender, about 10 more minutes. Serve immediately, sprinkled with more salt and pepper to taste, if needed. Leftovers keep well refrigerated in an airtight container for up to 5 days.
Notes
Make sure to wash the squash beforehand. As the skin is kept on, give the squash a good scrub with a brush.
Feel free to change the seasoning to whatever you like! Fresh herbs such as rosemary, thyme, or sage are a great alternative. For a savory squash, you can also try garlic powder, onion powder, curry powder, or chili powder. You can add some brown sugar or maple syrup for a sweeter roasted squash. Alternatively, you can use smoked paprika or cayenne pepper for a spicy-smoky flavor, as it pairs well with the sweetness of the delicata squash.
A sharp knife is a must to cut the squash in half safely.
Delicata squash is quite versatile, so you can pair it with various other ingredients to bulk it up! Try pairing it with some cheese such as feta cheese, goat cheese, mozzarella cheese, and parmesan cheese. You can also top the squash with nuts and seeds such as pine nuts, pistachios, pecans, walnuts, pumpkin seeds, and sunflower seeds. Sliced fruit such as apples or pears is a great addition as well.