The best walks and hikes in Dutchess County
4.6
(141)
1,913
hikers
69
hikes
New York? In this guide, we’ve reviewed our full collection of hikes and walking routes in Dutchess County to bring you the best hiking routes in the region. To see which of our walks in Dutchess County is the right one for you, browse real tips and photos uploaded by other hikers—and see what they had to say about each walk.
Last updated: October 25, 2025
5.0
(14)
213
hikers
1. Breakneck Ridge Trail loop — Hudson Highlands State Park Preserve
5.14km
02:09
350m
350m
Intermediate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.
4.6
(5)
110
hikers
Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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5.0
(6)
52
hikers
3. Sugarloaf Mountain loop — Hudson Highlands State Park Preserve
9.80km
03:23
410m
410m
Intermediate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.
4.5
(2)
14
hikers
4. Bald Hill Loop – Hudson Highlands State Park Preserve
15.8km
05:07
670m
670m
Expert hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
3.0
(1)
8
hikers
Expert hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
3.7
(3)
3
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
1
hikers
Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
1
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.7
(6)
141
hikers
9. Wobbly Stone – Forest Pond loop from Cornwall-on-Hudson
9.82km
03:41
480m
480m
Intermediate hike. Good fitness required. Mostly accessible paths. Sure-footedness required.
4.5
(6)
121
hikers
10. Walkway Over the Hudson loop from Poughkeepsie
6.11km
01:42
110m
110m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
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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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