1 pt. small heirloom variety tomatoes or grape tomatoes, halved
2 tablespoons olive oil, plus 1/2 c. olive oil, divided
1/4 tsp. kosher salt, or to taste
1 c. packed basil leaves
2 small garlic cloves, peeled
1/4 tsp. crushed red pepper (optional)
1 9" refrigerated pie crust, pre-baked according to package directions
1 c. shredded havarti cheese
1/3 c. crumbled goat cheese
2 tablespoons sliced almonds
1/2 c. arugula
Preheat oven to 425° F. In a large bowl, add asparagus, tomatoes, 2 tablespoons olive oil and kosher salt. Toss to coat vegetables with olive oil. Spread vegetables on a large, rimmed baking sheet. Roast about 20 minutes, or until vegetables are tender and slightly shriveled. Remove vegetables from oven; reduce temperature to 350° F.
Meanwhile, in a food processor, combine basil, garlic, and if using, crushed red pepper. Process until very finely chopped. Add remaining 1/2 cup olive oil; pulse several times until just combined.
Spread basil-garlic mixture on bottom of pre-baked pie crust, reserving about 2 tablespoons basil-garlic mixture for drizzling over tart. Top with roasted vegetables, Havarti cheese, goat cheese, and almonds. Bake 6-8 minutes, or until cheese has melted. Top with arugula; drizzle with reserved basil-garlic mixture. Serve warm.