The first frontier state to enter the Union was:

Tennessee
Vermont
Ohio
Kentucky
Louisiana

I believe it was Vermont

I am stuggling between Vermont, Tennessee and Kentucky

You can find that here:

http://www.50states.com/statehood.htm

The answer is still not clear.

There is a chart there with the dates when each of the states was brought into the Union. Check the states which you are not sure of. It will clarify.

It does not say which was first.

The answer is Vermont

To determine the first frontier state to enter the Union, let's gather some information. Since the website you provided doesn't mention the order of statehood, we'll need to explore other sources.

One reliable approach is to consult historical records or textbooks. Another option is to visit official government websites, such as the U.S. National Archives or the Library of Congress.

By conducting a quick search, you can find a list of states in order of admission to the Union. Here are the first frontier states from the list:

1. Kentucky (1792)
2. Tennessee (1796)
3. Ohio (1803)
4. Louisiana (1812)

From these options, Kentucky was the first frontier state to enter the Union in 1792. Therefore, Vermont is not the correct answer.