Naturally low in fat and nutrient dense, winter squash is a healthy substitute for the toast in the classic breakfast dish of egg-in-the-hole. There’s a beautiful assortment of squash available and you can use any variety of winter squash, although acorn is the best with its sweet and tender flesh. These squash are small and heavy when ripe, with a tough outer skin that’s eatable after cooking. I used the small sweet dumpling squash as I was drawn to its beautiful green striped skin. Use a sharp knife to cut the squash, as the skin and deep ridges can make it challenging to slice. You can pierce the squash a few times with a knife and microwave it on high for about 2 minutes, to soften the skin before cutting.
Pre-heat the oven to 425 degrees. Trim off 1/2 inch from each end of the squash and discard. Slice the remaining squash into thick rings, horizontally. Using a spoon, remove the seed and membrane from the center of each slice. Coat a roasting tray or baking sheet with cooking spray or a little bit of olive oil. Brush the slices of the squash with the olive oil and place on the baking sheet. Sprinkle with the salt, pepper and red pepper flakes. Bake the squash rounds for 12-15 minutes or just until tender.
Remove the baking sheet from the oven. Carefully crack an egg into each of the holes. Season the eggs with a pinch of salt and return to the oven. Reduce the heat to 375 degrees and bake the eggs until cooked through or cooked to your liking, about 10 minutes. Serve the eggs with the fresh thyme and bacon crumbles, if desired.