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Preheat oven to 425F. Place chicken thighs skin-side up on a rimmed baking sheet. Drizzle with 1 tablespoon olive oil; sprinkle with 1 teaspoon salt and ½ teaspoon pepper. Bake for 25 minutes.
Meanwhile, in a medium bowl, combine asparagus, tomatoes, lemon quarters garlic, lemon zest, and remaining 1 tsp. salt and ½ teaspoon pepper, tossing to coat.
Remove chicken from oven; add asparagus and tomatoes to baking sheet. Return chicken to oven; bake until chicken is golden brown and cooked through, about 20 minutes more.
Remove chicken from oven; let rest 5 minutes. While chicken rests, prepare Roasted Garlic-Lemon Vinaigrette. Spoon over chicken and vegetables.
In a small bowl, mash 4 roasted garlic cloves (from sheet pan) with a fork. Whisk in 3 tablespoons olive oil, ½ teaspoon salt, and ¼ teaspoon pepper until a chunky paste forms.
Whisk in 3 to 4 tablespoons lemon juice (from roasted lemons), 1 teaspoon honey, and ½ teaspoon lemon zest.