Combine the olive oil, vinegar, maple syrup, and mustard together in a blender; blend until smooth.
Arrange the endive on a serving platter with the rounded side down so that the leaves act as little bowls. Fill the endive with the diced pear, walnuts, and Gorgonzola cheese. Be careful to not overfill if you want to pass these. Carefully drizzle the dressing over the filling. Season with salt and pepper.