Combine first 3 ingredients; cover and let stand 30 minutes or until soft.
Drain in a colander over a bowl; reserve liquid.
Combine fruit and cinnamon; set aside.
Preheat oven to 42
Trim fat from pork.
Cut a 1 1/2-inch-wide horizontal slit through the center of the pork to form a pocket using a long, thin knife. Stuff the apricot mixture into the pocket using the handle of a wooden spoon to help push the apricot mixture to the center of pork.
Place the pork on a broiler pan; insert meat thermometer into thickest portion of pork.
Combine sugar, ginger, salt, and pepper.
Pour 1/2 cup reserved liquid over pork; sprinkle with sugar mixture.
Bake at 425 for 20 minutes. Reduce oven temperature to 325 (do not remove pork from oven); bake at 325 for 25 minutes. Arrange the squash around pork.
Bake at 325 an additional 45 minutes or until the thermometer registers 160 (slightly pink), basting pork with remaining liquid every 15 minutes.