• Where:  Southeast Dutchess County, NY and adjoining Connecticut.

• 45 miles, hilly  (3300 vertical feet, hill index 4.2). 

 - - 49 miles with Variation A.

 - - 31 miles, hill index 3.9, if finish at Dover Plains and use Metro North train to get back to the start (Variation B).  This requires obtaining Metro North bicycle permit in advance. 

 - - 60 miles, hilly, with the finish to Brewster station. 

• Highlights:  Lots of beautiful scenes on quiet back roads.  

Ken Guyer introduced us to this gem.  It's a good example of the kind of rides you can experience by joining the Mid-Hudson Bicycle Club.

• Characteristics:  One long hill, and lots of smaller hills.  Mostly quiet roads, but some high-speed / high-traffic segments.

Hill climbs:  Total uphill climbing is about 3300 vertical feet.  Longest climb is about 800 vertical feet at an average grade of 2.6% (including some short non-climbing "rest" segments) -- but one steep segment of this on Quaker Hill Rd goes to about 7% grade for 150 vertical feet.  (see Measuring Hilliness).

Variation A:  This adds 200 vertical feet of climbing. 

Variation B:  If you end the route at 31 miles at Dover Plains, total climbing is about 2100 vertical feet). 

finish to Brewster:  This adds about 1100 vertical feet, including about a section of 150 vertical feet at about 8% grade and another section of 100 vertical feet at 7%. 

Downhills:  There are some long steep downhills.

Traffic:  We've found this to have somewhat lower traffic interaction risk than most other routes on this website.  We found the few segments on high-speed roads to be reasonably managable.

see Trip Reports | Road Condition Reports  

• warning:  Riding a bicycle on roads has dangers and risks that need to be taken seriously.  For more on those, see our page on risks.

More . . . 

• Directions to Start in Pawling: 

By train:  Take Metro-North (Harlem Valley Line) to Pawling.

By car: From Taconic State Parkway take Rt 55 East to Dutchess County Rt 69 (Dutcher Ave). Turn Left (north) on Dutcher Ave. and proceed to Main St in Pawling. Turn Right on Main, cross the railroad tracks, Left on Memorial Ave and then on to train station.

By car:  From Rt 684 North, continue on to Rt 22 North.  Then take Rt 55 West and turn Left on Dutchess County Rt 69 (Dutcher Avenue). Proceed as above to train station.

• Alternate starts:  Metro-North railroad station in Dover Plains, NY (This has the advantage of delaying the Quaker Hill climb until after a long warmup, and saves the best terrain till later in the ride).  or Kent, CT.

• Alternate finish:  Brewster NY.  An advantage of the Metro North train station in Brewster is that it has more frequent trains scheduled than the Pawling, Wassaic, or Dover Plains stations (as of July 2002).  The Brewster finish variation provides some quieter roads to continue on south from the normal finish in Pawling to the train station in Brewster -- though likely not easiest or fastest way, since it has some hills. 

It is tempting to go for the Southeast (formerly Brewster North) train station instead of Brewster.  But this adds two substantial unrewarding hills and more traffic. 

• Maps:  You should have detailed road maps of Dutchess County NY, Fairfield County CT, and Litchfield County CT to do this route (see Road Maps).  For the Brewster finish, also a road map of Putnam County NY. 

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