Apart from the fact that it looks like you're using HP-UX and not linux from the commands and ouptuts given, here's a few words.
The destination host appears to be '11.255.23.xx' (you don't specify), and your own host 'Boston' appears to be on the same subnet.
You shouldn't need to add a gateway for local network traffic.
However, using '255' as part of your network address is just wrong, and I'm amazed it works *at all!*.
The usable range of byte values in an ip address range from 1-254 (in a standard network environment). Usually the values 0 and 255 are reserved for network/broadcast addresses and subnet mask's only.
If using smaller than 24 bit netmasks however, there can be other un-usable values.
The fact this works for a short period of time at all is the miracle.
One long-haired git at your service...
