Jester squash is an acorn-type squash, and acorn squash may be substituted for Jester. Both types are available in our farmstand.
Preheat oven to 375 deg. F. Wash the rind of 2 Jester Squash. Halve and seed the squash. Cover a baking sheet with sides with a piece of parchment. Place squash cut side down. Bake 45 minutes.
Meanwhile, prepare cranberry apple chutney. Mince 1 medium onion. Wash, core, and chop 2 large or 4 small apples. Peel and grate 4" piece of ginger root. Wash 2 cups cranberries. In a medium frying pan, heat 1 TB olive oil. Saute onion until translucent, about 3 minutes, before adding chopped apple, ginger root, and cranberries. Saute an additional 4-5 minutes until the cranberries begin to split. Add 2/3 cup brown sugar, 1/2 cup apple cider vinegar, and 1/4 cup maple syrup. Cook over medium heat until liquid is mostly absorbed and the ingredients in the pan are a consistency like a chunky applesauce, about 3-5 minutes further.
After squash halves are baked, turn them over and settle them onto the pan, pressing down a little so they are less likely to tip over. Pack cranberry apple chutney into and on top of the squash halves.
Return to oven and bake 15 more minutes. Serve hot. Enjoy!