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 425°.
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.
Place pork on a serving platter; cover with foil. Let stand 15 minutes before slicing.