HUDSON VALLEY RAIL TRAIL:
LLOYD-HIGHLAND, NEW YORK
-BIKE IT OR HIKE IT-
Last Updated; June 28, 2025
Length: Hudson Valley Rail Trail; 7 miles
On-road Connection to Wallkill Valley Rail Trail; 1.6 miles
Difficulty: Hudson Valley Rail Trail; Easy. Flat, paved rail trail.
On-road Connection to Wallkill Valley Rail Trail; Moderate. On-road hilly section.
Directions:
To start from the Route 299 parking lot in Lloyd [Western End]; From I-87 (NY State Thruway) take exit 18 to Route 299 east for 1.5 miles. Parking lot is on your right.
To start from Tony Williams Park in Lloyd [Central Section]; From I-87 (NY State Thruway) take exit 18 to Route 299 east. After about 2 ¼ miles, turn right onto New Paltz Rd (Route 12) and travel 0.7 miles to a left hand turn onto South River Rd. Turn right into Tony Williams Park. The trail starts to the left past the basketball courts.
To start from the Hudson Valley Rail Trail Depot parking lot in Highland [Eastern End]; From I-87 (NY State Thruway) take exit 18 to Route 299 east. After about 2 ¼ miles, turn right onto New Paltz Rd (Route 12). The parking lot will be located next to the right side of the road. You'll see a sign and a large pavilion.
To start from the Walkway Over the Hudson in Highland [Eastern End]; From I-87 (NY State Thruway) take exit 18 to Route 299 east. Head south on Route 9W through Highland. Just before the turn off for the Mid-Hudson Bridge turn left down Haviland Rd. The first parking lot on your left is for the HVRT.
The Hudson Valley Rail Trail runs along the former rail bed of the New York, New Haven & Hartford Railroad. The railroad used to cross over the Hudson River via the Poughkeepsie Railroad-Highland Bridge. This bridge, at 6,768 feet long and 212 feet above the river, was hailed as the longest railroad bridge in the world when it was completed in 1888. It served as the only Hudson River train crossing south of Albany, NY until a fire put it out of commission in 1974. The Hudson Valley Rail Trail travels West, from the Walkway Over the Hudson in Highland, to the Wallkill Valley Rail Trail in New Paltz. From the East Side of the Walkway Over the Hudson, the Dutchess Rail Trail travels Southeast, to Hopewell Junction. For more information visit; HUDSON VALLEY RAIL TRAIL .
The Hudson Valley Rail Trail is part of the Empire State Trail , which is a continuous 750-mile route spanning the state from New York City North, to Canada and Buffalo East, to Albany, creating the longest multi-use state trail in the nation.
Hudson Valley Rail Trail:
Starting from the Western End of the Walkway Over the Hudson in Highland; Restrooms, food vendors, water fountain, picnic tables, informational boards, Map Board, Walkway West Pavilion and the Walkway West Visitor Center are located here. Head West, along the paved Hudson Valley Rail Trail and you'll quickly come to the HVRT parking lot. An old 1926 red caboose and Map Board are located here. After traveling through a deep rock cut you travel through two tunnels underneath Mile Hill Rd and Route 9w. A Spur Trail at 0.6 miles leads to Route 9w. Next, a bridge takes you over Routes 44 & 55 bringing you to a small parking lot along Commercial Ave at 1.1 miles. Another Map Board located here, as well as, an old train signal. The trail travels North and opens up, as a fitness course follows alongside the trail. You'll come to the Hudson Valley Rail Trail Depot parking lot at 2.1 miles. A second 1915 red caboose is located here along with restrooms, a picnic pavilion and water fountain. Continuing along the trail you head back into the woods, underneath an old iron "Farmers Bridge" and through a deep rock cut. Travel through a tunnel underneath New Paltz Rd at 2.5 miles and cross into Lloyd. Look for an old RR Signal on your right at 2.8 miles. + See; RR Signal Below. Walk up to the top of the small knoll behind the signal light and turn right. Then walk 18 paces (2 steps = 1 pace) along the knoll up a small hill. A large boulder will be to your right, but you head left 14 paces along the edge towards a stone wall. This should bring you to a double-trunked tree shaped like a V on the opposite side of the wall. A large rock with white quartz should be on top of the stone wall. Just below this rock, remove 2 small rocks blocking a cavity in the wall. Under a flat rock used to keep the box secure is the Hudson Valley Rail Trail Letterbox. Continuing West, along the trail, you'll pass by a silver pole and RR Rail Holders on your left. + See; RR Rail Holders Below. Come to a side trail at 3.1 miles for the Black Creek Water Trail. The Black Creek is a Class A protected trout stream and access is a fairly easy scramble down the embankment. Finally you travel along a high berm with steep drop-offs before coming to Tony Williams Park parking lot at 3.5 miles. Map Board, playground, picnic tables and restrooms located here. Nice views of the rolling hills and Illinois Mountain on your left. The trail then travels through a tunnel underneath S Riverside Rd, followed by a rock cut and a second tunnel underneath New Paltz Rd. Cross a bridge over Black Creek at 3.9 miles in New Paltz. Look left at 4.5 miles to spot some old iron RR Rail Holders. Come alongside Route 299 and pass by the Route 299 parking lot at 5.2 miles. Map Board. Cross-light over South St. Come to Ohioville Rd at 6.4 miles, where two cross-lights get you to the Northern Side of Route 299, as the trail continues West. Cross over I-87 and come to Putt Corners Rd after 7 miles. This is the start of the Henry W. Dubois Greenway Connector, which connects the Hudson Valley Rail Trail to the Wallkill Valley Rail Trail.
Henry W. Dubois Greenway Connector:
[Continuing Mileage] Head right, North, along Putt Corners Rd following a BIKE LANE. Turn left, West, down Henry Dubois Dr, which I believe now consists of a 2-Way SEPARATED BIKE LANE. This is a hilly road. Come to Chestnut St (Route 32) ,where a crosswalk takes you over busy Chestnut St, to a paved trail connecting you to the Wallkill Valley Rail Trail after 8.5 miles.
Old Railroad Equipment:
+ RR Signal:
Railroad
Signals direct the engineman on how to proceed. They are categorized into
two levels: Permissive and Absolute. Permissive signals alert train operators
there is an obstruction on the tracks ahead. They are considered
“permissive” because their function is to protect. After the stop, they can
continue forward at a slower speed, commonly referred to as the “restricted
speed.” An absolute signal occurs at any point of the track where there’s an
interruption. They are considered “absolute” because their function is to
control. When a train reaches the absolute signal, it must come to a complete
stop and stay stopped until the signal indicates it’s safe to proceed. There
are different types of Railroad Signals. Semaphores consist of blades,
set to different positions, while Light Signals use different color
lights/number combinations.
+
RR Rail Holders:
RR Rail Holders were used to store extra
railroad track alongside the train tracks. Usually made of iron or concrete, the
top is shaped like a small U to keep the tracks from falling off. I
assume these were used to keep the rails off the ground and quickly available if
needed. Couldn't find any information on them.
HH
CLICK HERE FOR HUDSON VALLEY RAIL TRAIL MAP
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