Styles of touring
There are several styles for doing a multi-day bicycle tour:
Camping out and carrying it all -- Perhaps this is the purest style, but we've never tried it. Our concern with choosing this style for the Hudson Valley is that the extra weight will encourage choosing roads that avoid hills. Often this means major roads which miss the places that make the Hudson valley special.
Credit card touring -- Just carry clothes, drink, and repair tools. Use the credit card to take care of lodging.
Light and fresh credit card -- Reserve each lodging place, and then send a package to each one in advance -- with toiletries and a fresh change of clothes for the next day.
Supported tour -- Somebody else with a motor vehicle takes your spare clothes, repair tools, and stuff to the next night's lodging. If you get in trouble along the way, the vehicle comes and rescues you. There are two important variations on this: (a) Organized tour guide services -- where you pay them money, (b) Informal support, where friend or family drives ahead and visits museums and shops, and you carry cel phones -- and you pay some other way.
Breaking it onto days
Four days -- Possible breakpoints are (1) around Tomkins Cove or Bear Mountain; (2) around Poughkeepsie or Hyde Park; (3) around Tivoli or Germantown.
Three days -- Obvious breakpoints are (1) between Bear Mountain and West Point (like the Bear Mountain Inn, or in Fort Montgomery or Highland Falls); (2) Rhinebeck (near Rhinecliff on the map).
Two days -- The obvious breakpoint is around Poughkeepsie or Hyde Park.
One day -- Can it be done? By a strong rider with very good endurance training on the right long summer day? Yes of course.
Shuttling back between finish and start
A major challenge for organizing a one-way bicycle tour is how to get back home after you reach the finish. If you've managed to arrange the "supported tour" style, then this is included somehow in the package. Otherwise, there are four major options:
Train -- Amtrak has stations in New York City and Albany, and regular service between the two cities. But be sure to check directly with Amtrak for their latest rules about transporting bicycles.
Bus -- There is likely a bus service, but we don't know much about it. The obvious place in New York City where the buses come and go is the Port Authority terminal in mid-town.
Rent a car one-way.
Just keep ongoing.