A fun-filled ride

Challenging climbs, descents and spectacular scenery awaits.

How to get there

The signed trailhead is located at the East Branch Community Trails parking area, which is located on NYS Route 9N, in the Town of Keene, 3.5 miles north of the intersection of NYS Routes 73 and 9N in the Town of Keene. (Coordinates: 44.305097, -73.789526)

By the numbers

  • Level of difficulty: Intermediate
  • Route length: 15.1 miles (24.3 kilometers)
  • Elevation gain/loss: 1,554 feet (474 meters)
  • Smooth pavement, gravel, and dirt roads. Due to rain runoff and winter road maintenance practices, sand and small stones can be washed over any of these surfaces.  While this is most prevalent in the spring and early summer, storm events can deposit debris onto the road surfaces at any time of the year

A quiet route that will test your abilities

This challenging intermediate ride starts with a gentle descent over a smooth, wide shouldered and quiet state highway. Savor this time that gets you warmed up for what’s about to begin. Once you leave the state highway and turn onto the Upper Jay Trumbull’s Corners Road you have a bit of work to do as you begin a four-mile climb. The hardest part of the climb occurs at the end, along Rivers Road (aka Anthony Rivers Road). This nearly mile-long road starts off as pavement but changes over to gravel as the grade increases. The gravel portion will test your ability to maintain solid traction as you climb steeply over a 10% to 14% grade.

From here you begin the next segment of your ride - a super fun and stunningly beautiful loop around Upland Meadow, Styles Brook, and Jay Mountain Roads. Upland Meadow is a fun gravel and dirt road that takes you through the forest to Styles Brook Road. Turning left you make your way to an open meadow, with babbling Styles Brook on your right. Looping around the meadow you continue to climb and then descend quickly to the start of the loop. It’s then back over Upland Meadow Road (totally worth doing again) and back onto Styles Brook Road. This time you turn right and briefly pass through the forest and across a wetland before reaching a spectacular bit of farmland. It is spectacular, complete with a historic farmhouse and barns, and stunning views of mountains in the distance; a most unusual sight for being high up a mountain.

Take a break, take some pictures, and savor the views before continuing because your attention will be fully on your descent down paved Styles Brook Road back to New York State Route 9N.  This descent is the real deal; it’s steep, and loose stones and sand can be found on the road at any time of the year. Speed control will be your focus before making your way back to the highway and your car, which is located a little more than half a mile down the road.

Additional Information
This route can be shortened by turning right off Upland Meadows Road instead of left and descending directly to New York State 9N, but it’s worth the extra loop and double dose of Upland Meadows Road.


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Due to limited cellular coverage, please be sure to download this route and save for offline use before you leave home.

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