Pre heat the oven to 375 degrees and line a sheet pan with foil.
Peel the butternut squash and cut the butternut squash just above where the squash begins to flare out.
Using a small spoon, scoop out the seeds and pulp as you would with a pumpkin.
Using a pastry brush, brush 2 Tablespoons of the olive oil inside the squash and over the outside.
Roast the squash in the 375 degree oven for 25-30 minutes or until the squash is just fork tender but not mushy!
Remove the squash from the oven and cool.
Reduce oven temperature to 350 degrees.
To make the couscous filling.
Place the dried cherries in a small bowl and cover with warm water. Set aside.
In a large saucepan, heat 2 tablespoons olive oil over medium high heat. Add the couscous and stir for 5 minutes to toast the couscous.
Add the garam masala and cook for another minute.
Add the vegetable stock and bring to a boil. Cover and reduce the heat to a simmer.
Simmer for 10 -15 minutes or until all the stock is absorbed and the couscous is all dente - tender but still firm.
In a medium skillet over medium high heat, add the remaining 2 tablespoons of oil. Add the shallots and cook for 5 minutes or until the shallots are tender and lightly browned. Add the spinach and cook for another 3 minutes or until the spinach is wilted.
Drain the cherries and add them to the spinach mixture.
Add the couscous and stir to combine.
Add the pepper and sherry vinegar and stir to combine.
If serving right away, add the pistachios and stir.
Taste and add additional salt and pepper as needed/desired.
Fill each butternut squash with the couscous mixture.
Place on the foil lined sheet pan and re heat in a 375 degree oven until the squash is heated through. Serve.
If making ahead: Complete through adding the sherry vinegar and pepper. Refrigerate the bowls and couscous. Let come to room temperature before reheating and stir in the pistachios just before filling the bowls. Re heat filled bowls in a 350 degree oven for 15 minutes until heated through.