The Top 5 Attractions around Pawling
There are plenty of places to see and visit around Pawling. Whether you love hiking or cycling, Pawling is a region where 5
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: November 6, 2025
Maybrook Trailway
Highlight (Segment) • Trail
Amazing stretch of the EST!
Passing the lake and along side old train tracks, wide open skies await you while passing on the trail through 'the great swamps'.
Passing the lake and along side old train tracks, wide open skies await you while passing on the trail through 'the great swamps'.
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Whaley Lake
Highlight • Lake
Whaley Lake is the largest lake in Dutchess County. So nice to ride here!
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Wetlands Along Maybrook Trailway
Highlight (Segment) • Natural
This paved rail trail traverses two counties in New York — you can bike more than 28 miles on it if you go from end to end.
This particular section …
This particular section …
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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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Most popular routes around Pawling
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