|Browsing the FAQ link below may be of some help. Generally speaking 32 bit programs will run fine under 64 bit Windows. If Oregon Trail is 16 bit then you are out of luck.|
You may need to install it under a Windows compatibility mode. Assuming it is 32 bit. Use Window help to learn how.
After Googling Oregon Trail 3 I assume it is 32 bit as it appears to be circa 2007. So install under a compatibility mode.
If you need to use external hardware to play OT that might be a problem but the same rules apply.