Wassaic to Poughkeepsie via 3 state, 5 counties & 3 mtns

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  • Wassaic to Poughkeepsie via 3 state, 5 counties & 3 mtns
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General Information
Way Points: 

Wassaic RR Station> 81> Clark Hill Rd> Skiff Mtn Rd > West Woods #2> 4> East St> Lucas> Jackson> White Hollow> Salmon Kill Rd> 41/44, Salisbury, CT> 41> Mt Washington Rd, South Egremont, MA> Cross Rd> 344> Copake Depot> 344> 7A, Copake, NY > Empire St> 82> Salt Point Tpk> Poughkeepsie RR Station

Interest Tags: 
Fred Steinberg
Signature Route : 
Vertical Gain: 
Difficulty Rating: 
5 out of 5
Attached Files

This route requires determined riders who need to be diligent with their time as the first section is hilly and slow, the overall distance is great and limited hours of daylight are cut by 2 hours of riding time on trains each way. Plus, prevailing westerly winds tend to generate headwinds in final 2 legs. 5500' vertical gain on full route. 

Hardpack sections in first leg till climb up Mt Washington Rd, MA Includes bailout option to Wassaic (81 mile total ride). However, trains run from Wassaic every other hour. Includes 3 options in first leg: 1- Clark Hill Rd, shorter and steeper. 2- Avoids Clark Hil Rd, is 1.6 miles longer but not as steep. 3- Avoids all the hilly, hardpack roads, not adding additional mileage. An essential point to remember about this ride is to keep moving. Check your hour of sunset. You do not want to be traveling the final stretch in waning light. Rt 82 & the Salt Point Tpk runs into the setting sun. You may not be visible to passing drivers with the sun behind you. You will need a time cushion in case of mechanicals. I think eating lunch in Salisbury is too soon into the ride. Copake Falls may not have the selection that La Bonne Market has but it is at a better place in terms of time and distance (56 miles) into the ride. There are no real hills past Copake Falls. Mind your cue sheet and read road signs in the hilly section in the first leg: Clark Hill/Kinbloe Hill to Rt 4. You will not be the first cyclist to get lost if you don’t pay attention. West Woods #2 goes all the way to Rt 4 but turns a few times to get there. Do not miss the next turn, onto East Street when you are descending Rt 4 in the first leg. Also on the first leg 2 turns after East Street, Lucas is very easily missed as it doesn’t look like much of anything and is poorly marked, if at all. You should be looking for this one on your cycle computer. Free town water is had in Salisbury. You will make a right off Salmon Kill Rd onto Rt 41/44 as on the cue sheet. The water fountain is just at the first left. You will see a big stone tub next to the white Salisbury Town Hall. Turn the spigot and fill your bottles. In the final leg, Rt 82 from Pine Plains to the Salt Point Turnpike has an iffy shoulder. Caution must be exercised. This may not be the place to rotate a paceline.


Fred Steinberg


HS 11/24/2023

HS 4/3/15

cycling trips