The best road cycling routes around Highland
4.6
(43)
890
riders
69
rides
Last updated: October 10, 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.
Sign up for free
9
riders
3. 1889 Rail Bed Trail loop from Highland
67.6km
03:17
590m
590m
Intermediate road ride. Good fitness required. 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.
5
riders
5. Amazing View Of The Shawgunks – Walkway Over the Hudson loop from Poughkeepsie
173km
08:43
2,370m
2,370m
Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
Get access to more routes and recommendations from other explorers.
Sign up for free
Already have an account?
Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
Most popular attractions around Highland
Get inspired with the komoot mobile app
Explore more
Browse the best Road cycling routes in other regions.
Get ready to conquer new peaks
Sign up for Free