2-3 days in advance: Make cookies. Prepare and roll out dough. Using cutters from set, cut 4 large trees, 2 small trees, 3 train engines (flip 1 before baking), 5 trucks (cut off cabs to make train cars). Bake and cool.
Outline tree and train cookies using tip 6 and full-strength royal icing; flow in using thinned royal icing. Let dry 24 hours on waxed paper-covered boards.
Pipe details using full-strength royal icing. Outline and fill-in windows; pipe tip 3 zigzag tree trunks, tip 6 dot headlights, tip 2 and tip 1 outline wheels and spokes. Let dry. Use melted candy to attach 2 Lollipop Sticks to each cookie. Let dry.
Bake and cool 2-layer cakes (bake 1 1/2 in. high layers for 3 in. high cakes).
Tint fondant: 32 oz. green, 24 oz. blue. Prepare cakes and cover with blue fondant. Roll out green 1/8 in thick. Use plates from stand to mark sizes; cut fondant to cover tops of plates and attach with Piping Gel, trimming as needed. For hills, cut 1 3/4 in. wide strips: one 19 in. long for 6 in. cake; two 13 in. long for 8 in. cake; two 16 in. long for 10 in. cake. Cut wavy top edge; attach to cake sides using damp brush. For tracks, mark 2 circles, 1 in. apart, on cake tops; begin outer circle 1/2 in. from outer edge. For ties, use Cake Dividing Wheel to divide 6 in. cake into 16ths, 8 in. and 10 in. cakes into 12ths (add an additional line in between for 24 lines). Cover marks using black FoodWriter. Pipe tip 6 message.
At party: Position cakes on stand. Position cookies. Pipe tip 6 bead borders.
* Combine Leaf Green with Lemon Yellow for lighter green shown.
* Combine Christmas Red with Red-Red for red shown.
* Combine Violet with Rose for violet shown.