Harlem Valley Rail to Millerton to Connecticut
  • Where:  northeast Dutchess County and Litchfield County Connecticut -- starting near the Metro North train station at Wassaic.
  • 29 miles, moderate hills, (1600 vertical feet, hill index 3.5) 

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For a much longer route, 61 miles, see Harlem Valley Rail to Trail to Falls

For an 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 "connect" at mile 24.1 to join the Quaker Ridge route and finish at the Metro North train station in Pawling (total 46 miles) or even Brewster (total 60 miles).  

  • Highlights:  Rolling quiet roads with beautiful farms in Dutchess county and Connecticut, and a section on the nicest off-road "rail trail" around.  A tour through a different world -- but reachable by train from Manhattan.
  • Characteristics:  Moderate hills.  Two sections on an off-road paved "rail trail".  For both the main route and the variations, traffic interaction is typical of (or perhaps lower than) most other routes on this website.

Hill climbs:  Total climbing around 1600 vertical feet.  Three substantial climbs:  the toughest almost 150 vertical feet at a grade around 8% (see Measuring Hilliness), another of 300 feet but spread gently over 2 miles, and one of around 100 feet with a rest in the middle.

Traffic:  The main route normally very little high-speed and/or high-volume motor vehicle traffic.  About 7 miles have traffic which is more than low, but often less than moderate.  The rest of the road segments often have low traffic.  4.4 miles are off-road on the Harlem Valley Rail Trail.

see Road Condition Reports - Trip Reports  

more . . . 

  • Directions to Start at Amenia -- trailhead of Rail Trail: 

by car:  Coming from the west:  From the Taconic State Parkway, go East on Route 44 to its intersection with Route 22 at the traffic light in Amenia (along the way, can use Route 44A to bypass Millbrook).  Coming from the south, can take Rt 684 to Rt 22 to its intersection with Rt 44 in Amenia.  Then from the traffic light in Amenia, go East on Rt 343 about a quarter mile, then turn Right onto Mechanic St and go about a quarter mile to the Amenia trailhead -- at the corner of Mechanic St, Railroad Ave, and Depot Hill Rd.  See the Harlem Valley Rail Trail website for more details on directions and parking.

  • Directions to Start at Wassaic train station parking lot: 

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 November 2003, parking is free on weekends.

Alternate starts:  Millerton, Sharon CT.

  • Maps:  You should have a detailed road map of Dutchess County to do this route (see Road Maps). 
  • Connections to other routes: 

Quaker Ridge goes within 0.9 mile of this route at its southern reach near the Ten Mile River train station.

Hills and Horse Farms of NE Dutchess meets this route in Millerton and at Sheffield Hill Rd. 

Berkshire Loop goes within about 5.4 miles of Millerton.  But the shoulders on high-speed Route 44 between Millerton and Salisbury are narrow or non-existent at some points, though often reasonable.  There are at least two other connecting routes, between Sharon and Salisbury, with less motor vehicle traffic. 

 Map of Route Route Directions Cue Sheet Trip Reports and Road Condition Reports Photos Tourism More Routes 

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