Here’s how I got it to work on Windows 10:
-Download Windows 1996 version (240.8 MB) of the game.
-Unzip folder with 7-zip or something similar.
-Open The_Amazon_Trail_Win_ISO_EN, open Game Files, then mount AMAZONtrail (the ISO file) using Daemon tools light (which is free to download and use). You can double click and choose to open with Daemon tools or drag the ISO file onto the Daemon tools shortcut on your desktop.
-Once the image is mounted in a drive, instead of clicking on the auto play pop-up window to choose what happens with the disc, ignore the pop-up, go to File Explorer, scroll down in the sidebar until you see the AMAZONTRAIL disc in one of your drives, single click it then scroll down to AMAZON32 (an Application file).
-This next step is optional, but it makes the game more fullscreen: Right click on AMAZON32, click Properties, click the Compatibility tab, and under Settings check the boxes for Reduced color mode (8-bit 256 color) and Run in 640 x 480 screen resolution.
-Select Apply and Ok, then double click AMAZON32.
It ran for me immediately, I didn’t even have to install it.

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In reply to Ashley Tucker.

Although 1.5 has a 32-bit executable. vs 1.1 & 1.2. Does not work with windows 64-bit. Due to 16-bit executable setup.exe. That is why it said installer not found.

Windows 10 made quite a departure from windows 8.1 by removing win32’s so it might be possible that it is having compatibility
issues locating it’s configuration. by Microsoft removing ancient win32’s.
But try this if it is still works at all with windows 10 64-bit.
E:INSTALLSETUP.EXE (To force installation of the game).

also once it is installed under
E:INSTALLSETUP.EXE

open auto play again with the little amazon music pops up
you will see start amazon trial 3rd edition.
that is the other way to install this. the install option should work.

In reply to Micah Wright.

I tried getting the 3rd Edition game to work by using Daimon Tools (which I am not too familiar with to begin) but every time I try to install, the little amazon music pops up and a window that says ‘installer not found.’ What do i need to do to get it to work? I actually have the original disc as well somewhere, but never could figure out how to get the game to play on Win10. Do you know how to get it to work on Win10? Thank you!

Hi all Micah here this is the newer version of the game The Amazon Trail 3rd edition Ver. 1.5 (known as 1999 edition)

https://archive.org/download/tested-64-bit-learning-creative-for-vista_202008/Tested%2064-bit%20Learning-Creative%20Installation%20Originals/Premiere%20Multimedia%20%2B%20Trial/Amazon3.iso

So linking for newer windows