Pour 6 cups chicken stock or bone broth into a large skillet.
Add 2 cups pearl barley and turn the heat up to high. Give the mixture a stir.
Once the liquid starts to boil, turn the heat down to simmer.
Cook barley, stirring occasionally, for 25 minutes. Cool and move to a large bowl.
Cut off the ends of the 8 mini cucumbers and slice the whole cucumbers in half lengthwise. Chop the cucumber halves into pieces. Set aside in a small bowl.
Cut off the ends of 1 red onion and peel the onion. Chop the onion into small pieces.
Drizzle 1 teaspoon olive oil into a medium-sized skillet and set to medium heat.
Add 2 cups cherry tomatoes and season with ½ tablespoon dried oregano, 1 teaspoon salt, and ¼ teaspoon black pepper. Stir to coat tomatoes in oil and seasonings.
Cook tomatoes, stirring occasionally, for 10 minutes. Tomatoes will have softened and some will have split open. Remove the skillet from the heat.
Top barley with cucumbers, red onion, ½ cup kalamata olives, 1 cup crumbled feta cheese, and 1 cup balsamic vinaigrette. Use salad tongs or a large spoon to toss everything together.
Finally, top Greek barley salad with warm, seasoned tomatoes. Serve with Lemon wedges if desired.
Notes
When pearl barley is done cooking, it will have an al-dente texture and the pearls will have doubled in size.
To save time, the pearl barley can be prepped in advance. Cooked (and cooled) barley can be refrigerated for 3-5 days. Just add the toppings and dressing when you are ready to serve.