CliffordK

A lot depends on what you're interested in. One day events? Multiday events? Organized rides? Disorganized rides? BUDGET?

For example, in Oregon:

Cycle Oregon is one of the most popular multi-day rides in Oregon. It is a reasonably well supported multi-day ride, and relatively expensive.

On the flip side:

Pedalpalooza is more of a conglomeration of local Portland bicycle events during the summer, most of which are FREE.

You could knock out two states in a day or two with the annual STP ride.

Aside from the big events, here in Eugene, there are just daily/weekly rides one can join such as the Eugene Gears Rides. Here are the January 2016 rides scheduled, and all free if you wish.

You could snag a few states if you do the RAAM, although it may not be the choice for the casual rider.

There have been some people that have done a challenge to do the top 50 or 100 hill climbs across the USA. Not necessarily organized events, but there are published lists of mountains.

If I was you, either choose big supported events like Cycle Oregon or Ragbrai (iowa), or select a region, then post on the regional subforum. Then pick out several smaller regional events you can hit over a week or two in the summer such as the Portland Pedalpalooza, interspersed with other rides. The Portland area C&V group often also does a ride during Pedalpalooza. Or, maybe choose a dozen big multi-day tours, and then also do smaller local events to fill in.

If you're already planning on flying, I wouldn't ignore Hawaii. There may be some winter events.

Do you have a folding bike? S&S Coupled bike?