LapLink lets you use the parallel port without having to configure TCP/IP stuff. It's raw bytes, more like a really fast null modem cable.
But why bother getting the right cables (I have some, easy to DIY, but you can't buy them off-the-shelf anymore) and software (some piracy required I imagine). Instead you can use RS232 at 115.2kbps. Google did the arithmetic and unit conversion for me:
160 Megabytes) / (1125 (bytes / second)) = 1.64609053 days
Zmodem is pretty slow, but ZedZap/8K-Zmodem is pretty quick and easy to find software that supports it for DOS, Win9x and Linux. If you do not require error detection and flow control, then Xmodem is fast. (recommend you use a null modem cable with flow control RTS/CTS wired, this is almost always wired correctly with off-the-shelf cables). Don't need a 16550 UART for this to work, an 8250 is adequate if you have flow control enabled.
I'd highly recommend you send ZIP files over your link rather than uncompressed data. If you have enough disk space free, you can use pkzip's multivolume support and archive the entire disk into several managable files. (rar's is even easier to use than pkzip's)