Double Pugsley: Wassaic to Southeast

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  • Double Pugsley: Wassaic to Southeast
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General Information
Way Points: 

Wassaic Metro North railroad platform(start)> Harlem Valley Rail Trail> Cascade Rd> Smithfield Valley Rd> Sn Fri Rd> Pugsley Hill Rd> Leavitt Rd> N Mabbettsville Rd> Little Rest Rd> Killearn Rd> Chestnut Ridge Rd> Dover Furnace Rd>  Sherman Hill Rd> Berkshire Rd> Dogtail Corners Rd>  Bulls Bridge Rd> Dogtail Corners Rd> Duell Hollow Rd> Quaker Lake Rd> Quaker Hill Rd> Rt 55 west> Harmony Rd> Maple Rd> Cornwall Hill Rd> Bullet Hole Rd> Pugsley Rd> Southeast Metro North railroad platform(end)

Interest Tags: 
Brian Sullivan
Signature Route : 
Vertical Gain: 
Difficulty Rating: 
5 out of 5
Attached Files


This ride connects Pugsley Hill Road (at the north end of Dutchess County) with Puglsley Road (at the very south end of Putnam). Between are many fabulous miles of hardpack dirt roads traversing the farms and orchards of the Harlem Valley. Don’t be fooled by the distance covered, 65 miles: with almost half of that unpaved and close to 100’ elevation gain per mile, this is a big, peak season A route.

Two planned food stops: a deli at mile 19, and a gas station convenience store at mile 40. If time and conditions allow, make the second stop your longer one; purchase food & drinks at the Bulls Bridge store, then cross back to the west side of the Housatonic. Just past the covered bridge find the trailhead on your right, and walk down to the sculpted riverside rocks and eat your lunch there. It’s a magic spot.

Other highlights include challenging early dirt climbs up Cascade Mountain and Pugsley Hill; the glorious descent of Ridge Road; and skirting the Taconic ridge on Duell Hollow and Tracy Road.

Recommended tires: 28c or larger




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