Preheat the oven to 300°F (150°C).In a small bowl, stir together 3 tablespoons extra virgin olive oil, 2 tablespoons sugar, 2 cloves garlic (grated), 2 teaspoons dried oregano, and 1 teaspoon salt. Use less garlic or leave it out for a milder flavor.
Cut 1 pound cherry tomatoes in half and place them cut side up in a single layer on a baking pan or medium baking dish. Don't overlap them.Spoon the seasoned oil evenly over the tomatoes.
Bake at 300°F (150°C) for 1½ hours, until the tomatoes are soft and lightly caramelized.Spoon the pan juices over the tomatoes before serving. Enjoy on toast, pasta, grain bowls, or salads.
Substitutions
Cherry tomatoes → Grape, date, or small plum tomatoes all work well. The riper the tomatoes, the sweeter the flavor.
Extra virgin olive oil → Regular olive oil works too, though the flavor won't be quite as rich.
Garlic → Omit it if preferred, or use garlic-infused olive oil for a milder flavor.
Dried oregano → Swap with dried thyme, marjoram, Italian seasoning, rosemary, or fresh thyme.
Sugar → Use honey, maple syrup, or a pinch of brown sugar.
Salt → Kosher salt or fine sea salt both work well.
Optional finish → Try balsamic glaze, lemon zest, fresh basil, black pepper, or red pepper flakes before serving.
Tips
Use ripe tomatoes: They'll be sweeter, juicier, and more flavorful.
Keep them in one layer: Don't overlap, or they'll steam instead of roast.
Grate the garlic: It melts into the oil and coats every tomato.
Don't skip the sugar: It balances acidity and helps the tomatoes caramelize.
Roast low and slow: A low oven keeps the tomatoes juicy and concentrated.
Save the oil: Drizzle the tomato-infused oil over toast, pasta, salads, and more.
Store in the fridge: Let cool completely, then refrigerate in an airtight container for up to 6 days.