Multi-Variant Routes Routes with Dirt Roads

GrNY SGS – Pawling

For the fourth and final week in the GravelNY Spring Gravel Series we start and end in Pawling, NY in the Harlem Valley and ride some of the best dirt roads in Dutchess County (NY) and Litchfield County (CT).

Short Distance Group

  • 46 miles
  • 3,650 feet climbing

Long Distance Group

  • 65 miles
  • 5,360 feet climbing

Add-on options for people taking MetroNorth

Because the trains only run every two hours to/from Pawling and people taking MetroNorth may want to get home more quickly or ride additional miles, there is an add-on route which you can take to get to Brewster where the trains run every hour. It utilizes the Maybrook Trailway, which opened in 2021…

  • +14 miles, ~600 feet of climbing

Highlights Include…

  • River Road along the Housatonic River
  • Macedonia Brook State Park (long distance group)
  • Pawling Nature Reserve

The Route

All the routes start and end at the Pawling MetroNorth station with the option to ride to Brewster using an add-on route.

Route Details

These routes involve considerable riding on dirt roads so 38-53mm tires are recommended. Strong riders may be able to do the ride on 32-35mm tires.

We’ll meet up at a bakery near the Pawling MetroNorth station and then ride east over to Connecticut where we’ll spend most of the day. Along the way we’ll hit a couple dirt roads – Tracy Road, Game Farm Road, and Meeting House Road before getting to Sherman Connecticut.

After going through Sherman, we’ll take some quiet roads over to the New Milford River Trail (gravel) which goes along the Housatonic River. When we get to the end of the trail we’ll continue along the Housatonic on River Road (also gravel).

River Road along the Housatonic River (photo by Cyclo Saurus)

We ride River Road for quite a while until we get up around Gaylordsville where we go up a short, steep hill (2/3rds of a mile w/ an average grade of 9.4%) on Front of the Mountain Road which is a dirt road. At the top of that hill we get onto Long Mountain Road which take us most of the way back down the hill we just climbed.

You’ll then take Mud Pond Road (also gravel) and then take quiet paved roads to Kent where there are a number of options for lunch.

The additional segment for long distance riders

Shortly after Kent the long distance group heads off to do a 19 mile loop up to Sharon, CT. The loop starts with ~7 miles of climbing, but the grade is a relatively gentle 2 1/2 to 3 percent, and much of the climb is on gravel as you go through Macedonia Brook State Park on Macedonia Brook Road and Keeler Road.

Keeler Road (photo by Cyclo Saurus)

If it’s open Ellsworth Hill Orchard & Berry Farm is worth a stop for a snack. Then the long distance group heads back to Kent. On the way back they’ll ride on Modley Road (gravel). There is an additional stretch of gravel which is gravel – North Kent Number 1 Road and River Road – but the hill on North Kent Number 1 Road is incredibly steep and treacherous, so we opt to go down the hill on Skiff Mountain Road (paved) instead.

The shared route back to Pawling

Going south from Kent both groups take Schaghticoke Road (gravel) along the Housatonic River down to Bulls Bridge Road where we take a small diversion to go see Bulls Bridge – which is a historic covered bridge.

After Bulls Bridge we cross back into New York and there are about 5 miles on paved roads to get to get to Duell Hollow Road which is gravel. That gets us back close to Pawling and it’s a few miles to get back to our starting point.

Duell Hollow Road (photo by Cyclo Saurus)

At the end of the ride we’ll gather at O’Connor’s Public House for a little socializing (as time permits).

The Add-On Route To Brewster

Because trains to/from Pawling typically only run every two hours, if you need to get back to the City on MetroNorth and you’ve missed a train (or you just want to ride more miles), you can take one of the two add-on routes that will get you to Brewster where trains generally run every hour.

Both routes take you over to the Maybrook Trailway, which is quite beautiful in spots and just opened in 2021.

The Maybrook Trailway

The only difference between the two versions is that one does a short bit of gravel along the way.

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