The best road cycling routes around Poughkeepsie
5.0
(11)
417
riders
41
rides
Last updated: October 21, 2025
5.0
(1)
43
riders
1. 1889 Rail Bed Trail – Walkway Over the Hudson loop from Poughkeepsie
119km
05:56
1,230m
1,230m
Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
26
riders
2. Walkway Over the Hudson – 1889 Rail Bed Trail loop from Poughkeepsie
61.1km
02:57
450m
450m
Intermediate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.
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17
riders
3. Dutchess Rail Trail – Walkway Over the Hudson loop from Arlington
23.3km
01:07
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5
riders
4. Upper Landing Park – Walkway Over the Hudson loop from Poughkeepsie
137km
06:50
1,490m
1,490m
Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
3
riders
5. Roadbike loop from Arlington
48.2km
02:29
510m
510m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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