I’ve made a bunch of buildings, but now I’ve decided to try and build a castle. Buuut destroying all my buildings will leave huge, ugly holes everywhere…
So is there anyway to start a new settlement, but transfer over the hearthlings I’ve loved and raised?
Not really. Did you used the floor tool? If so, destroying a building will restore the ground and its grass.
I did the same thing in my map. I used a bunch of small improvised “slum” houses for each hearthling, and then when I finally got all I needed, I started removed them and replacing with the actual planned houses I had in mind.
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I used the floor tool in buildings, but all my pathways are going to leave hug holes 
Oh well, I’ll just need to make a new world I guess!
Could someone who’s played the game more than I have confirm if roads don’t bring back the ground when deleted? I thought they did, but I wouldn’t be surprised if they don’t.
If a hearthling dig the ground automatically as result of a building going there, it will be recovered when you delete the build.