I have heard really good things about the 5BBC's Montauk Century Ride which is on May 15th this year. I have never done the ride and wondered if the people here thought it is as good as the word of mouth.
The Montauk Century is a great ride and the 5BBC does a really good job running a somewhat complicated event. There are 3 primary ride options, but even these have further options regarding where you can check-in. Go to the website 5bbc.org and you can review all the options and sign-up right there online. It's a great course and hopefully the ride will be blessed with glorious weather like last year.
I did a ride called "Ride to Montauk" last June.
From Penn station to Montauk, approx 145 miles around 8 hrs.
It had the exact same route as Montauk Century.
A little bumpy in queens but once you reached Long Island,
roads are flat with minimal traffic and you would fly.
There were 4 or 5 rest stops. Plenty of food and water.
At the end, they got shower, massage, free beer,
ice cream and a LIRR ticket home. I will do it again this year.