The Top 6 Attractions around Wingdale
There are plenty of places to see and visit around Wingdale. Whether you love hiking or cycling, Wingdale is a region where 6
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
hidden gems are waiting to be explored and visited. Check the top places to visit in the region and plan your next adventure today.
Last updated: December 2, 2025
Whaley Lake
Highlight • Lake
Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
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River Trail
Highlight • Viewpoint
This well-maintained dirt road is great for biking, especially int he autumn when the fall leaves transform the trail. The road takes you right up to the water with excellent views of the Housatonic River.
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Tracy Road Gravel Route
Highlight (Segment) • Trail
Well kept and secluded gravel road
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Gas station to refill water
Highlight • Rest Area
I ran out of water prior to passing Whaley Lake. There was NOTHING around to refill. The next town is miles away and far off the EST.
This gas station …
This gas station …
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Bulls Bridge
Highlight • Bridge
This is one of three old covered wooden bridges spanning over the Housatonic River. While the one at Cornwall is still intact, the original Old Covered Bridge in Sheffield was destroyed by fire and had to be rebuilt.
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