• where:  northeast Dutchess County and southeast Columbia County, NY, and a section in Litchfield County, CT -- starting from the Metro North train station at Wassaic.

• 59 miles, moderate hilliness, (3900 vertical feet, hill index 3.8) 

• mapping:  digital mapping resources + GPS . . .

GPX file with all tracks + key waypoints : [ map on Bikely | Google Earth KML | GPX ]

• variations

Variations A + B avoid the longest hills (58 miles, 2700 vertical feet, hill index 2.9) 

Variation C continues on north to the village of Hillsdale, with hills (70 miles).

Variation D takes it further to explore quiet roads + hills in the north end of the valley (80 miles).

For a much shorter route (30 miles) which uses some of the same roads, see Harlem Valley Rail to Millerton to Connecticut. 

For a much easier route in this area, see Amenia to Millerton - Rail Trail and Roads.

An option of interest to riders using the Metro North trains might be to use the "connection" at mile 58 to join the Quaker Ridge route and finish at the Metro North train station in Pawling (total 77 miles) or even Brewster (total 92 miles).  

• highlights:  Endless rolling quiet roads with beautiful farms in Dutchess and Columbia counties.  Climb to the biggest views from a Dutchess county road.  Lunch in a quiet village.  Ride sections on the nicest paved "rail trail" around.  Take a side trip to visit Bash Bish Falls, the prettiest waterfall in the Berkshires.  All this accessible by train from Manhattan.

One of our favorite rides.

• characteristics:  Moderate hilliness.  At least one section on an off-road paved "rail trail".  For both the main route and the variations, traffic interaction is typical for routes on this website.

Hill climbs:  Total vertical climb around 3900 feet.  The longest climb is 550 vertical feet (McGhee Hill / Skunks Misery Rd).  Fortunately the average grade of this climb is less than 4%, but it starts with a steep 50 foot section around 9%.  There are two climbs around 150-200 feet at about 7-8% grade.  (see Measuring Hilliness)

Variations A+B avoid the bigger two of those hills, but keep the steep climb of about 150 vertical feet at 7-8% grade (just north of Sharon CT).

Variation C adds about 900 feet to the total vertical, including a hill with about 400 vertical feet of closely linked climbing (on North Rd), with much of that at 7-10% grade.

Variation D adds about 1600 feet to the total vertical, including the steep North Rd hill, and also a hill with about 230 feet of climbing mostly less than 6%. 

Traffic:  The main route has about 3 miles of high-speed and/or high-volume motor vehicle traffic.  Also about 2 miles of moderate traffic; and about 12 miles of traffic which is more than low, but often less than moderate.  The rest of the road segments often have low traffic.  4.5 miles are off-road on the Harlem Valley Rail Trail.

see [ Road Condition Reports ] - [ Trip Reports ]

• warning:  roads change -- but we have not checked much of the main route since the date below.

And it might have been a longer time since some of the Variations of the route were last checked by us.  Some roads and intersections might be different since then, or closed -- so be prepared to find alternatives -- a good reason to carry a detailed map. Other people may have more recent experiences with parts of the route which could help prepare: see the Reports page linked below.

Route not checked by us since 2010 -- learn more | see 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: 

By train:  Take Metro North (Harlem Valley line) to Wassaic.

By car:  The Wassaic train station is right next to the east side of Route 22 in western Dutchess county.  The station is about 3 miles South from the intersection of Routes 44 and 22 in Amenia NY.  Wassaic station is about 19.5 miles North from the intersection of Routes 55 and 22 in Pawling NY.  As of July 2001, parking is free on weekends.

Alternate starts:  Amenia, Millerton, Copake Falls, Sharon CT.

• maps:  You should have a detailed road maps of Dutchess County and Columbia County to do this route (see Road Maps). See also digital mapping resources above.

places: Hudson river valley, New York state, NY

bicycling: bicycle bicycling bike bikes bicycles bicyclist cycle cyclist cycling touring riding rider riders

routes: route routes ride rides tour tours turn cue sheet sheets map maps

Cue Sheet | Map of route | Trip Reports | Road Condition Reports 

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