How To Roast Cherry Tomatoes with Garlic & Herbs

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a fool-proof recipe to roast cherry tomatoes perfectly every time withs lots of garlic and fresh herbs

yield: 2 lbs roasted cherry tomatoes

  • Prep Time: 5 minutes
  • Cook Time: 1 hour
  • Total Time: 1 hour 5 minutes


  • 2 lbs cherry tomatoes
  • 3 heads garlic, ends trimmed+discarded
  • 4 sprigs fresh oregano (or other herbs like thyme and rosemary)
  • 1 ¼ cups olive oil
  • 1 tsp kosher salt
  • 15 cracks fresh black pepper


  1. Preheat the oven to 375°F.
  2. Add the cherry tomatoes, heads of garlic (cut-side down), and fresh oregano to a large 12” cast-iron skillet. Cover with the olive oil, salt, and black pepper. Toss well to combine.
  3. Roast for 1 hour and 30 minutes, or until the tomatoes are soft and caramelized.


  • Skillet size and cook time will vary if you cut this recipe in half or double it. Use a 10” skillet for about 40-45 minutes if you cut the recipe in half and 2 (12”) skillets for 1 hour if you double it. You always want a fairly even layer of cherry tomatoes to fit the bottom of the skillet.
  • All ovens are different, so use your senses to tell if the tomatoes are done – they should be soft, caramelized, and blistered.
  • The heads of garlic essentially turn into roasted garlic. To use it, squeeze out the soft garlic cloves and discard the roots/skins.
  • The olive oil becomes infused with tomato and garlic flavor. Save it for drizzling over eggs, dipping bread into, making sauces, tossing with pasta, etc.