4-Day Columbia County: New York to Hillsdale to Dover Plains

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Way Points: 

South & North County and Putnam Trailways>Pawling. Pawling>Rte. 20>Old Rte. 22>Rte. 22>Harlem Valley Rail Trail>Millerton >back roads & rail trail>Hillsdale. Hillsdale>Chatham>Stockbridge>Hillsdale. Hillsdale>back roads>Madava Farm>Dover Plains Train Station>NYC

3 out of 5
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Vertical Gain: 
Carol Waaser
Signature Route : 
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This is a really beautiful 4-day tour with roughly 50-60 miles per day, although the third day can be shortened to 40 miles.  (The third day is very hilly, so B and C riders will probably want to do the shorter route.)  Days 1 & 2 have about 35-40 vertical feet per mile of climbing, Day 4 has about 45 vertical feet per mile, so they are all about typical for a B ride.  On Day 3, the short route has 85 vertical feet per mile, and there are some dirt roads, so this is a much more challenging ride.  (I did not do the longer Day 3 loop, so I cannot say how much climbing would be encountered during the extra miles.)  These altitude gains were taken off my Garmin unit on the actual ride, so I believe they are pretty accurate.  I did this tour in 2013.

 The trip begins on the #1 train to 231st St., where there is an elevator to take your bikes down to street level.  Now that the Van Cortlandt Park restrooms on Broadway at 241st St. have been completely renovated, that’s a convenient pit stop at the start of the ride.  Much of the first day is on rail trails, as is part of the second day.  We stayed the first night at Pawling House, an historic house that was a stop on the Underground Railroad.  It’s a walk of less than a mile into town to an excellent restaurant for dinner.  There’s a covered back porch for the bikes.  The 2nd & 3rd nights we stayed at Sylvanus Lodge in Hillsdale, a plain vanilla motel but very cyclist-friendly.  There’s a garage to store the bikes.  It’s a short walk into town to several good restaurants (and a Stewarts for ice cream & sundries).

 The 3rd day is all about beautiful cycling.  Since it's just a loop ride, you won't be carrying any gear.  The loop goes up to Chatham, where you can have lunch, then over to Stockbridge and back to Hillsdale.  We decided to shorten the loop since we had done so much climbing before lunch (including a couple of short 13-15% grades).  You can create your own loop ride for this day.  Ours had a good stretch of dirt road (Wolf Hill Rd.).  We missed the turn onto Pheasant Lane (which is also dirt) and thus did a different route than the cue sheet.  But the roads have enough traffic that you can ask directions and find your way.  The scenery is stunning.

 On the 4th day, we cycled down to Dover Plains and visited the Crown Maple Syrup processing plant at Madava Farms (http://www.crownmaple.com/crown-maple-farm).  It was an interesting tour of the plant, with a maple syrup tasting, and we had lunch at their cafĂ©.  After lunch, the staff suggested that we take the Jeep track through the woods to get to Ridge Rd. and on to Dover Plains train station.  It was somewhat difficult on road bikes because of loose dirt & rocks (we had to walk a couple of short sections) but the scenery was well worth it.  Trip ends with the train from Dover Plains back to Grand Central. On the way to the Farm, on county road 24, Hall’s Corners Rd., there is a 15% grade for a short distance – but don’t worry, you can always walk.

 GPS links:

Day 1 - https://ridewithgps.com/routes/33505426

Day 2 - https://ridewithgps.com/routes/33505434

Day 3 (long) - https://ridewithgps.com/routes/33505450

Day 3 (short) - https://ridewithgps.com/routes/33505517

Day 4 (to Farm) - https://ridewithgps.com/routes/33505556

Day 4 (Farm to Train) -  https://ridewithgps.com/routes/33505576

cw  11/13   Rev. 7/2020

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