Harvest Squash Soup and Grilled Cheese with Caramelized Onions and Tomato Jam

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3 ½ LB Squash (I like Buttercup, Acorn and Butternut)
7 T Olive Oil
3 Large Shallots, chopped
4 C Chicken or Vegetable Stock
2 ½ C Apple Cider
1 T Dry Mustard
¾ t Cumin
½ t Cloves
½ t salt
½ t pepper
½ C Maple Syrup

Cut squash in half and drizzle with 3 T olive oil.  Put on a sheet pan, cut side down and roast at 425 degrees for 40 minutes or until soft.  Let cool to touch.  Sauté shallots in remaining olive oil until soft.  Deglaze pan with apple cider.  Add squash and stock and simmer for 30 minutes.  Add mustard, cumin, cloves, salt and pepper.  Puree in blender or with stick blender.   Stir in maple syrup and serve with garnish or your choice.  I like crab, chives or crème fresche.