Preheat oven to 400 degrees F. Line a baking sheet with a silicone mat or parchment paper.
In a medium bowl, drizzle tomatoes with olive oil and sprinkle with salt and pepper. Stir until tomatoes are coated. Transfer tomatoes to the prepared baking sheet and spread into a single layer. Bake for 15 to 20 minutes until tomatoes are slightly wilted and bursting. Remove from the oven and set aside.
While the tomatoes cook, bring a large pot of water to a boil. Season water with a generous pinch of salt. Cook pasta according to package directions until al dente. Drain pasta and run under cold water until completely cooled.
Add pasta to a large bowl and pour in avocado ranch dressing. Stir until pasta is completely coated.
Run a knife through the avocado flesh to make a checkerboard pattern, then run a large spoon under the avocado right up against to skin to remove the flesh. Add most fo the avocado to pasta bowl.
Add most of the crumbled bacon and roasted tomatoes to the pasta. Gently stir everything together until combined. Season with salt and pepper, to taste.
Sprinkle reserved bacon, avocado, and tomatoes on top of the pasta salad. Cover with plastic wrap and refrigerate until ready to serve.
I recommend serving this pasta salad immediately. If you need to make it ahead of time, don't go more than 4 hours to prevent the avocados from browning.