How to Access two different programs from PATH, both having same name in Windows 10?

Solution 1:

Since you specified "without altering the name of either", one possible solution is to make a link (see mklink) to the files somewhere in your path (or more preferably in the same folder as the original file) and that link can have a different name. Then you can use the name of that link to distinguish the two versions, but the file will still have its original name.

Example (run cmd.exe as an administrator - required for mklink):

mklink "python 2.7\python2_7.exe" "python 2.7\python.exe"
mklink "anaconda 4.1.1\python3_5.exe" "anaconda 4.1.1\python.exe"

CD \
python2_7.exe
python3_5.exe

Solution 2:

You can't if the two programs you want to run have the exact same name. What you are experiencing is how the PATH variable works. There shouldn't be a reason why you can't rename one program or other other, i.e. python -> python27 or python -> python35. Then you can reliably start either one.