Whaley Lake – Whaley Lake loop from Brewster Hill

Routes

Bike touring routes & trails

Whaley Lake – Whaley Lake loop from Brewster Hill

Moderate

2.6

(28)

riders

Whaley Lake – Whaley Lake loop from Brewster Hill

02:02

35.1km

180m

Cycling

Moderate bike ride. Good fitness required. Mostly paved surfaces. The starting point of the route is right next to a parking lot.

Last updated: October 28, 2026

Waypoints

Start point

Parking

Get Directions

5.30 km

Through the wetlands

Highlight • Cycleway

Great skies and good riding surface. Strong winds can be a challenge here.

Tip by

9.62 km

Maybrook Trailway

Highlight • Trail

offers possible resting spots with shade. good for people watching as well :)

Tip by

11.0 km

Beautiful trees and foliage along the Empire State Trail

Highlight • Structure

14.2 km

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 …

Tip by

17.3 km

Whaley Lake

Highlight • Lake

Whaley Lake is the largest lake in Dutchess County. So nice to ride here!

Tip by

17.6 km

Whaley Lake

Highlight • Lake

Whaley Lake is the largest lake in Dutchess County. So nice to ride here!

Tip by

29.1 km

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'.

Tip by

35.1 km

End point

Parking

Way Types & Surfaces

Way Types

35.0 km

167 m

< 100 m

Surfaces

34.7 km

408 m