Plan with
Confidence
Path Type
Loop
The Prosper Trail begins at the Prosper Road Trailhead on the eastern edge of Marsh-Billings-Rockefeller National Historical Park and climbs steadily through a quiet, shaded forest. The route follows a well-defined path through mixed hardwoods, passing through occasional rocky and rooted sections. After a moderate ascent, the trail intersects with the historic carriage road system—stay right at the junction to continue toward The Pogue.
From this junction, the route continues on wide, gently graded roads to reach the edge of The Pogue, a 14-acre manmade pond nestled below Mount Tom. The water is non-potable, but the area offers scenic views and good chances to spot deer, woodpeckers, and birds of prey. In fall, the forest canopy turns vibrant with color. Return the same way or extend the loop via other carriage roads.
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