The best road cycling routes in Dutchess County
4.9
(104)
2,022
riders
298
rides
Last updated: October 8, 2025
5.0
(13)
152
riders
1. Dutchess Rail Trail – Walkway Over the Hudson loop from Hopewell Junction
55.6km
02:20
340m
340m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(8)
131
riders
2. Upper Landing Park – Dutchess Rail Trail loop from Poughkeepsie
45.0km
01:57
220m
220m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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5.0
(2)
94
riders
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(2)
68
riders
4. Bear Mountain Bridge – View of Storm King Mountain loop from New Hamburg
100km
04:56
1,220m
1,220m
Expert road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(4)
125
riders
5. Whaley Lake – Maybrook Trailway loop from Hopewell Junction
79.4km
03:12
420m
420m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
45
riders
6. Old Hopewell Junction Station loop from MacDonnell Heights
43.7km
01:43
180m
180m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
43
riders
7. Dutchess Rail Trail – Walkway Over the Hudson loop from Crown Heights
62.8km
02:53
510m
510m
Intermediate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3.5
(2)
34
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
3.5
(2)
32
riders
9. Wassiac Rail Station loop from Wassaic
32.0km
01:42
190m
190m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(1)
58
riders
10. Old Hopewell Junction Station – Whaley Lake loop from Hopewell Junction
45.8km
01:52
240m
240m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.
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