Heat olive oil in a large skillet over medium heat. Add onion, carrot, and celery, and sauté until softened, about 5 minutes.
Add minced garlic and cook for another minute until fragrant.
Increase heat to medium-high, add ground beef, breaking it apart with a spoon. Cook until browned and no longer pink.
Pour in red wine, scraping the bottom of the pan to deglaze. Reduce heat and simmer until the wine has mostly evaporated.
Stir in crushed tomatoes, salt, pepper, and Italian herbs. Bring to a simmer, then reduce heat to low. Cover and let simmer for 45 minutes, stirring occasionally.
Add milk and simmer for an additional 10 minutes. Adjust seasoning to taste.
While the sauce simmers, bring a large pot of salted water to a boil. Cook rigatoni according to package instructions until al dente. Drain and set aside.
Toss the cooked pasta with the bolognese sauce. Serve hot, sprinkled with grated Parmesan cheese.