Begin by boiling water in a large pot; once bubbling, add the whole wheat penne pasta. Cook according to package instructions until al dente—typically around 8–10 minutes—then drain. Rinse the pasta in cold water to stop the cooking process and prevent sticking, setting it aside to cool.

While the pasta cooks, take a fresh cucumber and slice it into rounds about half an inch thick. Use a small knife to carefully carve jack-o-lantern faces into each slice.

Grab a large Ziploc bag and pour in 1/4 cup of water along with the natural purple food coloring. Once the pasta has cooled, add it to the bag, seal it tightly, and shake gently until all the pasta is coated.

Let the pasta sit in the colored mixture for a few minutes. Afterward, open the bag and drain the pasta again, giving it another rinse under cold water.

In a spacious mixing bowl, combine the colored pasta with your prepared cucumber faces, chopped broccoli, halved cherry tomatoes, shredded carrots, and shredded cheese. Drizzle Italian dressing over the mixture and toss gently.

Cover the salad with plastic wrap or transfer it to an airtight container and refrigerate for at least two hours, or overnight for best results. Before serving, give it a good stir and add a splash more dressing if needed.