Bring a large pot of salted water to a boil. Add the penne pasta and cook according to package instructions until al dente. Drain and set aside.

In a small bowl, whisk together the olive oil, red wine vinegar, dried oregano, minced garlic, salt, and black pepper.

In a large skillet, combine the cooked pasta, cherry tomatoes, cucumber, bell pepper, red onion, and Kalamata olives. Pour the dressing over the pasta and toss to combine.

Transfer the pasta to a serving bowl and top with crumbled feta cheese and chopped parsley. Serve immediately.