In the container of a blender, combine the mayonnaise, maple syrup, vinegar, and sugar. Cover and blend on low speed. Gradually pour in the vegetable oil while mixing until fully incorporated. Taste and season accordingly with salt and pepper. Set aside.
In a large serving bowl, combine the lettuce, cherries, apples, goat cheese and candied pecans. Toss with just enough of the dressing to coat, then serve with the remaining dressing on the side.