Looking for a Challenge

bicycling the roads of the Hudson Valley

There's a wide variety of road bicycling challenges:

Riding to a far place

A basic challenge is to see if you can ride to some other place and back.  In its fundamental form, you start from a very familiar place, like your home.  Or it could be a town that you use as your regular place for starting rides (like Rhinebeck or New Paltz).  First you try to reach places close by, and then as you confidence, knowledge, and strength increase, you try to reach places further away.  You can develop a satisfying sense of mastery of an area in this way.

The "regular place" from which this website has the most variety of routes is New Paltz.  New Paltz is easy to reach by the New York State Thruway, and has routes with a wide range of distances and terrain.  Other likely choices include Woodstock, Rhinebeck, and Millbrook.  But really it's whatever feels like "home base" to you.

We have family in Kingston, so it became a natural "base" for us.  On the Thruway we had driven by the New Baltimore service area many times -- so we got the idea of seeing if we could ride to the town of New Baltimore.  We succeeded, and it was fun.  And that led to trying out different variations, different starting point, and with different riding partners over the years -- and it eventually turned into the In the Shadow of the Catskills route.


The classic quantitative challenge is to see how far you can go in one ride.  A first challenge could be 10 miles, then 25 miles.  What's nice about distance is that the human legs are usually good at being trained for it.  The simplest formula is to start with some distance you know you can do, and then once every week or two do a big ride which is 5-10% longer than the previous one.  And do some shorter rides in between.  

After 25 miles, people typically go for 50, and then 75 -- or sometimes 61 or 62 miles as a "metric" century (100 kilometers).  After that, some people make it their big challenge to try to ride 100 miles in a day.  Most people try these distance challenges as part of some bicycling event where drink and food and some other support is provided. 

This website has a variety of rides at many distances -- see Routes by Difficulty Category.  But there is no category for "long and gentle" routes.  The difficulty with going for pure distance in the Hudson Valley is that it's hard to go more than 25 miles anywhere without running into lots of hills.  So you can either do your measured-distance rides in South Jersey, or Delaware and Maryland -- or you can ride more interesting terrain in Hudson Valley and say that your  miles were tougher.

The "long distance" game can be played with much greater seriousness than anything on this website -- using approaches different than what we described above.  If you want to see how far some people take this kind of challenge, check out the New Jersey Randonneurs

Getting up a tough Hill

Another basic challenge is "conquering" a hill.  This offers a sharp distinction between success and failure, and often the reward of a fun downhill run.

You can start by finding out if you can ride up all the hills on a gentle-to-moderate route, and then all the hills on a route of moderate hilliness.

Then you may be ready to test yourself on one of the hills on our Climbs page.  But don't start with the "Devil's Kitchen" climb on Platte Clove Road.  Back when they had the Tour de Trump road races, several of the professional riders ended up walking on that one.

Then there are games like seeing if you can climb up some hill without using your lowest gears, or inventing strange routes to see how many big steep hills you can do in one ride.


This is a favorite challenge for lots of people.  But it's not one we know very well.  If you want to play with this one, we suggest getting involved with riders who are really serious about speed -- like one of the racing clubs.  

Survey the range

A worthwhile accomplishment is to ride in a wide range of areas in the Hudson Valley.  The Overview Map gives an idea of what that could mean.

Here's a list of moderate rides that provides a broad survey:

For strong road bicyclists who've been riding a lot, this set includes some longer and hillier routes:

Or there's the "follow the Hudson River" survey:

The Adventure of Exploring

For us, the most amazing thing about riding in the Hudson Valley is that it is possible to go to places you've never been before, with terrain and road conditions you don't know, the possibility of dangerous animals -- with the the risk of not getting to a safe and warm place before dark, or before the bad weather hits -- or even have your bike, or yourself, suffer serious damage and not finish the journey at all. 

Here's our "adventure challenge":  Make up one route of your own in each of these counties:  Dutchess, Ulster, Columbia, Greene.


  • You can go a long ways without seeing a store in some of these upstate areas.  It is possible to run out of food and water.
  • Sometime a key road in your plan has a different name.  Or it's not ridable.  Or it doesn't exist any more.  The alternate roads you have to take may be much longer and harder.  It may get dark, and cold, and wet before you get to your destination.
  • There are more hills in the Hudson Valley than you can imagine.  We usually check out our route ideas on some maps that show elevation differences, like the DeLorme Atlas -- so we can try to avoid at least some of them.
  • Don't be surprised when your cell phone doesn't work out there just when you need it most.

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