Guust

I just changed NY to New York and it all uploaded just fine.
You will now need to edit your locations to change NY to New York at GD > Multilocations > Manage locations.

I am guessing you are viewing your site in Chrome and you don’t have a SSL certificate installed.
Chrome no longer allows geolocation by non-secured sites for privacy reasons.

Set the GD Listings Map widget in the sidebar on the Listings page to a fixed pixel width instead of a 100% width.

You will have to add listings yourself or allow users to add listings.
With the Social Importer addon you can import listings from Facebook or Yelp.

Try changing the default category for the listings. It seems you have the Trail category as default category for each listing in the Trail CPT.
Instead of Trail [CPT] > Trail [cat] > Hikng [sub-cat], you might be better as
Trail [CPT] > Hikng [cat]
Why do you repeat the CPT and the category?

I can’t directly see anything wrong.
You should use New York instead of NY etc for the region, but that will not stop things.
I am guessing you already have created the categories you are trying to import to, and the multi-locations addon is activated.
I was able to upload the file without any drama into my test site, after changing categories to match the ones in my site.
We’ll need URL and WP admin details if we need to investigate more.

It looks like you figured out how to collapse them: Appearance > widgets > GD Home Map widget > Collapse child/sub categories ? > Yes

To hide the legend: https://wpgeodirectory.com/docs/common-styling-examples/#legend

We will need a URL too to inspect any code. Thanks.