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Jess, Computer Support Specialist
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Experience:  Computer Hardware & Software Specialist - 10yrs Exp, Web Designer & Developer
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Oregon Trail 5 cannot locate Oregon5.Dat . Make sure the Oregon

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Oregon Trail 5 cannot locate "Oregon5.Dat". Make sure the Oregon Trail 5 CD is in the CD-ROM drive
Hi, thank you for using I am glad to assist you today.

  1. What is your Operating System? XP/Vista/Windows 7?
  2. Have you installed the software already but got the error when you try to run it?
Customer: replied 6 years ago.
1. Windows 7
2. yes
Is the program still installed in your Windows 7 system? If so, please try this:

  1. Locate the program's shortcut icon in your desktop screen if there is one.
  2. Right-click on the shortcut icon
  4. In the UAC (User Account Control) window that opens, click on YES, OK or ALLOW to confirm the action.
  5. See if the error message is still appearing.

Customer: replied 6 years ago.
i don't get a User Account Control window
Ok. But what happened when you right-click on the Oregon 5's shortcut icon then click on RUN AS ADMINISTRATOR? Did the program load successfully this time?
Customer: replied 6 years ago.
Customer: replied 6 years ago.
no, i got the same error message
Do you have the Oregon 5 shortcut in your desktop screen? When you right-click on the shortcut icon, did you see RUN AS ADMINISTRATOR? What happens when you click on it (Run as administrator)?
Customer: replied 6 years ago.
the same thing as when i attempt to run it normally, same error message
OK. Please try to UNINSTALL the software completely from your Control Panel => Programs and Features.

After the removal, please restart your computer. After restarting the computer, re-install the software and then try to run it again as an ADMINISTRATOR.
Customer: replied 6 years ago.
the same thing happened
Do you have the CD of your Oregon software?
Please try to load the CD in your CD/DVD drive and try opening the program again. See if it will load normally this time.
Customer: replied 6 years ago.
i didn't run and it asked if i wanted to run the installer, i said no
Please RUN the installer when the disc wizard prompts you to. Then, do not eject the disc in the drive and then run the program after the installation is done. See then if the program loads normally.
Customer: replied 6 years ago.
same problem happened
Ok... Please follow the procedures from this link to install your Oregon 5 software in your Windows 7:
Customer: replied 6 years ago.
that didnt work either
Customer: replied 6 years ago.
that didnt work either

i've been doing everything exactly as you say
Ok. Please do these:

  1. Uninstall the Oregon 5 software
  2. After the removal, please run this CCleaner Cleanup Procedures:

    Cleanup with CCleaner

    NOTE: If you are using a program named Roboform, please do not proceed with CCleaner cleanup. Roboform Data will be removed by CCleaner.

    Please download the FREE version of CCleaner from this link:

    Download FREE CCleaner Here or this link

    After you download the free tool, install it and run the scans and tests. By default, it runs CLEANER to cleanup from all system mess which includes all unwanted files, temporary files, temporary internet files, orphaned files and more. Make sure that all this mess that the Cleaner program has detected is removed. This will free up some space in your hard drive while speeding up your system as well.

    Next, run REGISTRY Cleaner and fix the found problems. Run this REGISTRY cleaner several times and fix the issues until no issues will be found.

    In order to run the Registry cleanup mode, open CCleaner, then look at the left panel of the CCleaner window. Locate and click the Registry link there and that should give you the Registry cleanup mode. Then click on the Scan for issues button. When the scan reached 100%, click FIX issues to remove the errors from your system. Then click the Scan for issues again then FIX whenever issues are still found. When no issues are found, close CCleaner.

  3. After the cleanup, please LOAD the CD and then COPY the entire content of the CD to a folder in your hard drive like in your Desktop or in your My Documents
  4. Right-click on the SETUP.EXE file and then click on Run as Administrator to start the installation process.
Customer: replied 6 years ago.
Would OT5installer be right? I don't see a setup.exe.
YES. If that file is of "application" type, then that is correct. Please give it a try.
Customer: replied 6 years ago.
still no fix
The Oregon software was installed successfully, right? And the problem now is that it is giving you an error message about Oregon5.dat being missing when you try to open or run the program. Is this correct?

Please try to follow these steps:


You will need to be logged into your computer as an Administrator to perform the following fix.

  1. Download and save it to your desktop.
  2. Double Click on My Computer (Computer on Windows Vista and Windows 7)
  3. Double Click on C:\
    Note: If this folder say "These files are hidden" Click on "Show the contents of this folder."
  4. Double Click on Program Files.
    Note: If this folder say "These files are hidden" Click on "Show the contents of this folder."
  5. Double Click on The Learning Company.
  6. Double Click on Oregon Trail 5
  7. Drag the file that we downloaded to your desktop in step 1 from your desktop and drop it in the Oregon Trail 5 folder we just opened.
  8. Right Click on
  9. Left Click Extract All. The Compressed Folders Extraction Wizard Should Appear.
  10. Click Next.
  11. Find the area on this page that says "Files will be extracted to this directory:"
  12. In the box you will need to DELETE the very last part that says "\OREGON5"
  13. Click Next
  14. A confirm File Replace Window will appear. Click on Yes.
  15. Uncheck the box "Show Extracted Files."
  16. Click Finish.
  17. Close all open windows and attempt to run Oregon Trail 5.


I hope that helped.

Customer: replied 6 years ago.
ive already tried that
Customer: replied 6 years ago.
Relist: Inaccurate answer.
none of his solutions worked
What happened when you tried the last solution? Were you still getting the same error message?

Please try this:

  1. Open Computer (Click Start => Computer)
  2. Double click to open Drive C. Note: If this folder say "These files are hidden" Click on "Show the contents of this folder."
  3. Double click to open Program Files folder (Do you have Program Files there or Program Files(x86)?). Note: If this folder say "These files are hidden" Click on "Show the contents of this folder."
  4. Double click to open "The Learning Company" folder.
  5. Double click to open "Oregon Trail 5"
  6. Now, you should be in this path: C:/Program Files/The Learning Company/Oregon Trail 5
  7. Download this file and place it in the folder where you are now (C:/Program Files/The Learning Company/Oregon Trail 5). Here is the link:
  8. You should get a file named OREGON5.INI
  9. Copy and paste that file, or move the file by drag and drop to the Oregon Trail 5 folder (C:/Program Files/The Learning Company/Oregon Trail 5)
  10. When an option to overwrite file pops up, please click YES or OK to proceed to overwrite.
  11. Close all windows
  12. Restart the computer
  13. After restarting, try running your Oregon software.
Customer: replied 6 years ago.
I didn't get an overwrite option. It says "this program will uninstall Oregon Trail 5th edition from your hard drive. Click OK to continue
Ok. You MOVED the oregon5.ini file into the folder C:/Program Files/The Learning Company/Oregon Trail 5

Now, double click on the program's shortcut icon in your desktop to start or run the program.
Customer: replied 6 years ago.
still the same
Please check in your System. Do you have:

C:/Program Files


C:/Program Files (x86)?
Customer: replied 6 years ago.
Customer: replied 6 years ago.
Omgosh! The program was in Program Files (x86) and I moved it to program files and it WORKS!!!
Ok. Please check if you have this path:

C:/Program Files (x86)/The Learning Company/Oregon Trail 5

If you have that path, download this other file and move or copy it to the folder:
Jess and 8 other Computer Specialists are ready to help you
Customer: replied 6 years ago.
Actually, earlier today I requested a refund. I didn't doubt your knowledge. Its just that I read so many reviews about it not working that I wanted a refund and I was going to return the program to the store. How can I cancel the refund request?
Cool! I am glad that the program worked this time. Please do not forget to click the ACCEPT button to accept my answer if it helped.

Leave a positive feedback if you are satisfied.

Thank you for using JustAnswer.

Customer: replied 6 years ago.
I loved ver 2 two of this game when I was a kid; it started having problems from wear and tear after a few years. I found it in a box of stuff last year and tried in on this comp and no go, so I got the new version. Most people hate it cuz its almost just like ver 2, but thats what I like about it. Anyway, thank you so much! Will you still get paid after I hit "accept answer" even though I requested a refund earlier?
Yes, I got paid when you accepted my answer. Thank you so much for that. Thank you for giving a positive feedback as well.