The Esopus flows out of artificially created Winnisook Lake, at 2,660 feet (810 m) above sea level the highest lake in the Catskills, on the northwest slopes of Slide Mountain, the Catskills' highest peak, in the town of Shandaken, within 300 feet (100 m) of the West Branch of the Neversink River on the other side of the divide between the Hudson and Delaware watersheds, amid expansive forest.
At the source it is crossed by a small wooden footbridge, followed by Oliverea Road (Ulster County Route 47), which it immediately begins to parallel through the forest.

The stream's headwaters descend from there northward into Big Indian Hollow, dropping a thousand feet (305 m) in its first mile (1.6 km) with an average slope of 13 percent, a narrow and rocky mountains stream through this section.
Along it there are three waterfalls, the uppermost being 30-foot (9.1 m) Otter Falls, and Parker and Blossom Falls below.
At first trending westward, away from the road, a half-mile (800 m) below Winnisook Lake it returns to the road's side and receives its unnamed first tributary from the east, draining another of Slide's hollows.

Bending to the west northwest, the Esopus forms part of the boundary of the Big Indian Wilderness Area to its south as it receives Giant Ledge Stream from the north, draining that peak and Panther Mountain, the former meteor crater whose walls determine the creek's upper course.
Another half-mile further west, the Esopus receives its first left tributary, Hanging Birds Nest Brook, which drains the north face of Spruce and Hemlock mountains to the south.

From there the Esopus flows due northwest for its next mile, as the valley floor of Big Indian Hollow opens up and some cleared land begins to abut the stream.
After the Little Peck Hollow Brook confluence, it turns west and braids into several smaller channels for 1,200 feet (370 m), reuniting just before crossing under Eagle Mountain Road.
It receives, another eastern tributary, the Elk Bushkill, which drains Fir and Big Indian mountains to the southeast, just south of the Burnham Hollow Road bridge.
The Esopus then bends back in a northward direction.
Short braided sections return during the next mile, along with gravel bars along the banks.

Bending past more braided sections and bars, the Esopus reaches the small former hamlet of Oliverea 0.6 mi (1 km) further north.
Here McKenley Hollow Road crosses, in a section with retaining walls on either side of the channel, Another 500 ft (150 m) to the north, the similarly named tributary, carrying water from the steep slopes of Haynes and Balsam mountains to the west, joins the Esopus from the west as the stream's main stem turns northwest, further away from the road, then curving northeast with more bars and braiding marking a wider channel.
The Esopus flows out of artificially created Winnisook Lake, at 2,660 feet (810 m) above sea level the highest lake in the Catskills, on the northwest slopes of Slide Mountain, the Catskills' highest peak, in the town of Shandaken, within 300 feet (100 m) of the West Branch of the Neversink River on the other side of the divide between the Hudson and Delaware watersheds, amid expansive forest. At the source it is crossed by a small wooden footbridge, followed by Oliverea Road (Ulster County Route 47), which it immediately begins to parallel through the forest.
The stream's headwaters descend from there northward into Big Indian Hollow, dropping a thousand feet (305 m) in its first mile (1.6 km) with an average slope of 13 percent, a narrow and rocky mountains stream through this section. Along it there are three waterfalls, the uppermost being 30-foot (9.1 m) Otter Falls, and Parker and Blossom Falls below. At first trending westward, away from the road, a half-mile (800 m) below Winnisook Lake it returns to the road's side and receives its unnamed first tributary from the east, draining another of Slide's hollows.
Bending to the west northwest, the Esopus forms part of the boundary of the Big Indian Wilderness Area to its south as it receives Giant Ledge Stream from the north, draining that peak and Panther Mountain, the former meteor crater whose walls determine the creek's upper course. Another half-mile further west, the Esopus receives its first left tributary, Hanging Birds Nest Brook, which drains the north face of Spruce and Hemlock mountains to the south.
From there the Esopus flows due northwest for its next mile, as the valley floor of Big Indian Hollow opens up and some cleared land begins to abut the stream. After the Little Peck Hollow Brook confluence, it turns west and braids into several smaller channels for 1,200 feet (370 m), reuniting just before crossing under Eagle Mountain Road. It receives, another eastern tributary, the Elk Bushkill, which drains Fir and Big Indian mountains to the southeast, just south of the Burnham Hollow Road bridge. The Esopus then bends back in a northward direction. Short braided sections return during the next mile, along with gravel bars along the banks.
Bending past more braided sections and bars, the Esopus reaches the small former hamlet of Oliverea 0.6 mi (1 km) further north. Here McKenley Hollow Road crosses, in a section with retaining walls on either side of the channel, Another 500 ft (150 m) to the north, the similarly named tributary, carrying water from the steep slopes of Haynes and Balsam mountains to the west, joins the Esopus from the west as the stream's main stem turns northwest, further away from the road, then curving northeast with more bars and braiding marking a wider channel.
Esopus Creek