Cook freekeh according to package directions and set aside.
Heat oven to 400 degrees. Toss the squash with 1 tablespoon olive oil and maple syrup. Season with salt and pepper. Roast in the oven for 16-18 minutes. Remove and allow to cool.
Sauté kale with 1 tablespoon of olive oil and garlic for about 5 minutes. Season with salt and pepper. Set aside.
Mix all the dressing ingredients together in a bowl.
Assemble salad by tossing freekeh, squash, kale, nuts, cranberries, and dressing. Taste and adjust seasoning accordingly.