There was someone on the 5BBC who did that all the way from Penn Station to Montauk - unbelievable! Then again if I had a dog and family I'd be really tempted to do the same
I know a bunch of folks who have done the Penn Station to Montauk. They noted that ride through the city is very rough. I'm not big on riding in LI so I start at Babylon when I did it 2 years ago. I prefer my native NJ. I'm working on a Ride from Cranbury to Tuckerton (about 150 miles). There is nothing wrong with the ride (the stops were very good) I just like my rides better. ;-)