For the authentic 1994 experience, point your DOSBox configuration to the extracted folder and execute TYCOON.EXE . Troubleshooting
TTO.7z Format: 7-Zip Compressed Archive Primary Content: Transport Tycoon Original / Deluxe Game Files Overview TTO.7z
If running the original Windows version, you may need compatibility mode set to "Windows 95." For the authentic 1994 experience, point your DOSBox