Length: 17.4 miles

Elevation change: 1,137 feet

Nearby Towns: Pawling, Hopewell Junction

Begin and End: At the Empire State Trail parking area in Holmes, NY

DOWNLOAD THE MAP AND TURN-BY-TURN CUE SHEET

The Maybrook Trailway arrows through the heart of the lovely Whaley Lake area, a region of hills, rocky outcrops and marshlands in the lower Hudson Valley. For this ride, you’re coasting gently downhill along the trailway before leaving it for the Dutchess County backroads.

The combination of trailway and country roads means that the ride isn’t confined to the trailway, so you’re not retracing your route. And you’ll barely use any of your battery on the Maybrook segment, since it’s mostly (though slightly) downhill. Save the battery, and your leg power, for the return, which tackles a few more challenging hills, none of which should discourage you from this pretty ride.

Whaley Lake from the Maybrook Trailway segment of the Empire State Trail.

This part of the Empire State Trail opened on the last day of 2020, and so I’ve only ridden it in early spring, before the trees fill in and the plants in the marsh green up. So while the photos appear to show a grey landscape, I’m sure spring and summer riders will see more colorful scenery. 

The ride begins in the parking area for the Empire State Trail in Holmes, New York. From this lot (there are no public restrooms, btw), take the ramp down to the trail and turn right.

Follow the straight, level path through a part of the peaceful swamplands, where preserved railroad poles tilt in the swamp like the masts of sunken ships. Soon views of Whaley Lake open up on your left, with year-round lake homes edging the water.

The trail’s straight path is relieved by sharp-edged rock cuts and small waterfalls here and there.

The abandoned railroad track, from the former Maybrook line, winds between a rock cut north of Whaley Lake.

Leave the Maybrook Trail behind when you reach its intersection with South Green Haven Road — you’ll see a parking area across the street — and turn left. This is the on-road return leg of the loop, but the scenery is gently bucolic, the landscape unfurling in pastures of green grass.

There are a few challenging hills on this return, particularly on Eder Road; after all, you’ve spent most of your time on the Maybrook Trailway rolling downhill!

Note that road crossings here are few and far between, and there are no public restrooms. So when you set out, be prepared for any eventuality: spare tube in your pack, fully-charged smartphone, water in summertime and something to eat.

Also note that there are no posted rules against riding electric bikes on this section of the trail. (We’ve added an article about electric bikes and the Empire State Trail here.)

These notes are descriptive only. You should always use the RideWithGPS app and/or download the turn-by-turn directions (provided above) for precise navigation.

The Details:

Elevation change: 1137 feet up and down over the whole ride.

Direction: For best results, leave your car in the Holmes parking area then follow this route in a counter-clockwise direction.

Start and end: Holmes parking area for the Empire State Trail, corner of Route 292 and Holmes Road in Holmes, NY. (GPS: 41.523614, -73.647181)

Afterwards:

Travel northeast to Pawling, New York. McKinney & Doyle Corner Bakery and Fine Foods Cafe takes up two shopfronts on Charles Colman Boulevard, the main street in this small Dutchess County village. While the cafe doesn’t open until 4:00, you can still visit the bakery next door, for coffee and fresh-baked goods.

Let this description from the bakery convince you:

If you live in the village of Pawling, somewhere around 6:00AM each morning, the aroma of fresh baked goods may work its way into your home.
That’s the time that the first muffins and Danish pastries of the day start to come out of the ovens. 7:00AM see the first rush of early commuters getting a still warm from the oven breakfast treat and the most delicious fresh brewed coffee and cappuccino’s in the area. By 9:00AM, the bakery is chock full of hot, homemade breads, rolls, brownies, cookies, turnovers, scones, English muffins, cobbler, layer cakes, pies and tartes.”

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