Preheat the oven to 425°F. Line a baking sheet with parchment paper.
In a large bowl, toss the zucchini, squash, bell pepper, and cherry tomatoes with 2 tablespoons of olive oil, oregano, salt, and black pepper.
Spread the vegetables in a single layer on the prepared baking sheet. Roast for 25-30 minutes, stirring halfway, until the vegetables are tender and lightly charred.
While the vegetables are roasting, bring a large pot of salted water to a boil. Cook the penne pasta according to package instructions until al dente. Drain and set aside.
In a skillet, heat the remaining 1 tablespoon of olive oil over medium heat. Add the minced garlic and sauté for 1-2 minutes until fragrant.
Add the cooked pasta, roasted vegetables, fresh basil, and lemon juice to the skillet. Toss everything together until well combined.
Serve the roasted vegetable pasta warm, topped with crumbled feta cheese.