Soak and cook wheatberries in your preferred method. I used a rice cooker, and soaked them in hot water for an hour before running them through a brown rice cycle with 2 cups of fresh water and a pinch of salt.
Meanwhile, preheat oven to 425 degrees.
Slice squash in half and remove seeds. Microwave for 2 minutes to soften for cutting.
Cut squash into salad-size pieces and toss with brown sugar, salt, and olive oil.
Roast squash for about 45 minutes, until tender and golden on the edges.
Chop bell pepper and slice tomatoes.
Shake dressing in a jar until well mixed and toss dressing with all salad ingredients until well coated. Season with salt and pepper.
Serve warm or chilled.