Preheat oven to 450F. Toss squash with oil and fenugreek and season with salt and pepper. Arrange squash in a single layer in a rimmed baking sheet and roast until well browned and tender, 20-25 minutes, stirring halfway through roasting; let cool to room temperature.

Cook freekeh according to package directions in chicken or vegetable stock.

Drain freekeh, transfer to large bowl and let cool completely, about 15 minutes. Combine raisins and 1/4 cup hot tap water in small bowl and let sit until softened, about 5 minutes; drain raisins.

Toss squash, raisins, dressing, cilantro, and walnuts to bowl with freekeh and gently toss to combine. Season with salt and pepper to taste.