I came into this section of the forum seeking this very same topic as I am signed up for the 100 mile route on the Ride to Montauk, in June.
I'm a bit intimidated by the distance.
My longest single ride to date is 46 miles, a trip on the famous 9W route to the Palisades/Tallman Mountain.
My first year of riding I was commuting primarily, and riding 20 mile recreational rides on the weekends.
This year, I'm riding longer distances, and I'm surprised at how much this changes the gear alone.
If all goes well enough to Montauk, I will sign-up for the North Fork ride as well.
Come September, you all might be helping me plan my first tour.
New York City to Albany, New York. (my mom recently moved near Albany in the winter)
Looks to be about 160 miles, with Poughkeepsie right in the middle.
Can I do 80 miles, 2 days in a row?
These are the types of questions a budding cyclist might ask himself.