Poughkeepsie, R2R, Lenape Ln, Laurel Ldg, Undercliff, Castle Point, Lake Awosting, Hamilton, Overcliff, Glory Hill, Poughkeepsie

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  • Poughkeepsie, R2R, Lenape Ln, Laurel Ldg, Undercliff, Castle Point, Lake Awosting, Hamilton, Overcliff, Glory Hill, Poughkeepsie
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General Information
Way Points: 

Poughkeepsie railroad station> Hudson Valley Rail Trail, R2R, Lenape Lane, North Lookout Rd> Laurel Ledge> Undercliff> Trapps Rd> Castle Point Carriage Rd> Lake Awosting> Hamilton Point Carriage Rd> Trapps Rd> Overcliff> Oakwood Dr> Glory Hill Dr> Lower Duck Pond Rd> Pine Rd> R2R> Hudson Valley Rail Trail> Poughkeepsie railroad station

Interest Tags: 
Hank Schiffman
Signature Route : 
Region Name(s): 
Gravel Grinding, The Gunks
A, B
Vertical Gain: 
Difficulty Rating: 
5 out of 5
Attached Files

Note: there is a day usage fee riding in the Mohonk Preserve. Riders should check in at the booth to the right near the start of the Lenape ascent. Purchasing a season pass with the bike option contributes to the wonderful work they have been doing on maintaining their carriage roads.

This ride is mostly well-tended gravel carriage roads. If you are comfortable with gravel, you can ride this on a road bike with 25 tires, but why would you? A gravel bike is the way to go.

A very early train will afford you wiggle room to take the time to enjoy its many vistas: the Catskills, High Point in NJ, the Great Gap of the Hudson. Ideally, do this ride when you have good visability; certainly do it when you have adequate daylight. It is 11 miles till you get to gravel, and those same 11 miles to the train back in Poughkeepsie.

Water is available via a spigot at the Mohonk Gatehouse at the top of the Lenape climb; ask first. You can also access water at the Minnewaska Visitors Center, close by your Minnewaska out and back: carry plenty of fluids. Pocket foods are a must. New Paltz, too soon into your ride and too far to the train back on a full stomach, is your only access to buy anything.

There is nothing technical about this ride, just a few steeper sections, but you will need strength and stamina to do it justice. Have solid brakes to descend those few steeper sections; make sure your bike is mechanically sound.

Should you find you have too much on your plate by the time you reach Lake Awosting, instead of taking the first left off of the Lake Awosting Carriageway to access the lake  take the second left (it will avoid the ride around the lake), then follow the Lower Awosting Carriageway to the parking lot and either take the carriage road back to the route back, joining it just above Awosting Falls, or if you are pressed, get on 44/55 and ride the shoulder to 299, and on to New Paltz.

If you are driving to do this route, park at the R2R parking lot off Springtown Rd. You will have traded 22 miles of riding for driving in traffic...

Many thanks to John Z for having pioneered this route.

HS 6/30/2023


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