See if this helps to add DropDownItems or Items to a menu.
1 MenuStrip(with a "File" menu item)
Public Class Form1
Private myCoolFolder As String = "C:\"
Private Sub Form1_Load(ByVal sender As System.Object, ByVal e As System.EventArgs) Handles MyBase.Load
For Each myFile In My.Computer.FileSystem.GetFiles(myCoolFolder, FileIO.SearchOption.SearchTopLevelOnly, "*.*") '// get files.
FileToolStripMenuItem.DropDownItems.Add(myFile) '// add as DropDownItems.
' MenuStrip1.Items.Add(myFile)'// add as Category on Menu.
Next
End Sub
End Class