Science Fantasy Village/City Map - Making building and Terrains meld together

[Jobo]

Hello Everyone and thank you for the help!

New to the Guild and really drawing maps (or at least attempting to make quality ones). I wish I could move right into the question, but I feel a little context is needed. So I have been making a map in the past week for a village for my current game of Numenera that has just moved online. Anyway, the concept of the city is that it is a nomadic village built upon giant basically giraffe robots (Inspired by Horizon Zero Dawn's Tallneck. See one of the attached images for the inspiration). The landscape they are travelling through suppose to be a wide path carved through a forest or a wide grassland area (Think Eurasian Steppe).

Now onto the problem...

My problem that I have is that I am lost in terms of making the terrain meld together with the ground in a convincing way. The current drawing and everything was hand drawn and I am lost in finding a way to do the same with terrain. So as you can probably guess from the upload of my current map, I have used Wilbur to make a height map and color it, but it looks almost too real compared to the buildings/robot giraffes (see. context!). For additional info I am using Photoshop CS6 to draw everything so far.

I appreciate any guidance and assistance that can be provided. Thanks to everyone for their time in replying.