The headwaters of the River Esk are in the moorlands above Westerdale. This is the Esk itself, into which the Esklets flow. Many of the Esklets flow between the heather near Esklets Crag on Westerdale Moor.

One of the many Esklets on Cooper Hill that merge with the River Esk in the valley below. This Esklet flows into a ribbon woodland en route to its convergence.

Hunter's Sty Bridge is a scheduled monument with Historic England. it is a ribbed medieval bridge dating back to the late 13th century, restored in 1874 by Octavius Duncombe, son of the first Baron Feversham. It has a single arch that spans the River Esk at Westerdale. The arch is segmental with a span of nearly 6m and has a double arch ring. Four ribs support the arch from ribbed abutments.

From New Road, where it passes Carr House and climbs to the top of Castleton Rigg, a narrow isthmus of land connects the Rigg to Westerdale Moor. From here there is a perfect view across the wooded riverbank to that part of Westerdale Moor that has an ancient Field Stystem and Settlement, most of which is no longer visible.

The River Esk remains low-key as it passes around the north of Castleton at Castleton Bridge. The River is now in its middle stage and is meandering all along its valley. From the Bridge the lush green fields between the River at Esk Mill Weir and New Road are visible. These fields are often home to a number of seasonal fairs.

AT Howe Wath the River Esk enters Esk Dale. The Danby Railway is close by to the north and The Howe road passes over the bridge to make a bee-line to Danby.

Ainthorpe is an attractive village on the opposite bank of the River Esk to Danby Village. It is accessed via Ainthorpe Bridge, which spans the Esk. Picnic benches are found at the foot of the bridge, facing into the Esk and the wooded bank opposite.

Duck Bridge is a pack horse bridge and incapable of conveying modern traffic, which uses the ford at its side. During normal weather conditions the ford is a road, but when the Esk is in flood there is often a shallow covering of water. A recent improvement to the ford is the steel rail on its downstream side, installed following a fatal accident when a car was swept off the bridge during a flood.

At Lealholm the River Esk flows swiftly, having just completed its run along the Crunkly Gill, a shallow gorge just south west of Lealholm Village. The Bridge has a Grade II Listing with Historic England, and dates to the early 19th century.

At Lealholm the flow of the River Esk is deflected by Lealholm Side from north east to south east, at a ninety degree angle, and now begins its final stage, rushing to the North Sea at Whitby.

On the South West fringe of Lealholm, as the River Esk leaves the village there is a set of stepping stones across the River. Generally, the Esk is quite shallow here and crossing is straight forward. When the Esk is in spate, however, a safe passage across the Stones is non-existent.

From Lealholm Rigg fog can often be seen settling into the Esk valley below Sleights Moor. Valley Fog is caused by a temperature inversion, as where warm air passes above a valley and there is cold dense air below it. The cold air settles into the valley, condensing as it does so and produces fog.

There is a ravine to the south west of Lealholm, which is known as the Crunkly Ghyll (or Gill). The outflow from the gorge divides as it passes around three small river islands before entering Lealholm. The Ravine was formed during the last Ice Age when the Esk Valley was carved from its point of origin in Westerdale to Lealholm.

As the River Esk bypasses Glaisdale, rounding a large north loop it streams south and passes beneath the ancient Beggars Pack Horse Bridge, which dates to 1610. Immediately to the south west of the bridge is a more modern railway viaduct. The Bridge guards the entrance to the valley between Limber Hill Wood and East Arncliffe Wood, through which the Esk flows.

The River Esk is almost entirely rural and thus very clean. As can be expected it supports an abundance of wildlife, and is a spawning river for salmon. The river has many salmon leaps, some of which are artificially made to help them over some of the weirs found along the river. Kingfishers and otters also abound in Eskdale.

As with the River Ehen in the western Lake District so with the River Esk in the eastern North York Moors, the rivers have a healthy population of Salmon and also freshwater pearl mussels. The River Ehen in the Lakes, and the River Esk in the North York Moors are the only rivers in their respective counties where freshwater pearl mussels are found.

The Coast to Coast path enters Grosmont from the Egton Estate Road and soon encounters a ford and footbridge over the River Esk on the west side of Grosmont. The precise location is part way down a sharp u-shaped loop from which the Esk then returns to continue its easterly direction. At the lower end of the loop the Murk Esk converges with the River Esk, having wound its way around the south side of Grosmont and having its beginings on Goathland Moor.

The confluence of the River Esk and River Murk Esk occurs on the western fringe of Grosmont. A large acute loop between Priory Farm and The Alders resultis in a river island. A road bridge spans the eastern side of the loop and a footbridge spans the western side. The confluence of the rivers can just be seen from the road bridge by looking along the length of the river island. The Esk travels around the loop and the Murk Esk is subsumed by the Esk at the apex of the loop, at the south east of the island, shortly after it passes beneath the railway viaduct. The river on the west (left) of the loop comprises both the River Esk and the River Murk Esk.

From Aislaby there are terrific views across farmland meadows to Sleights Moor. In-between is the River Esk, which sometimes unveils early morning mist vaporizing into the atmosphere.

The River Esk concludes its 28 mile journey from the Esklets on Westerdale Moor to Whitby Marina and the North Sea. The Marina is tidal, and the tide reaches Ruswarp Weir, about 2 miles west of Whitby.

At night time the illuminations of the boats and shops become a dazzling display of lights and reflections. The Esk Bridge at Bridge Street is the most northerly bridge on the Esk.

The bright lights of the West and East Piers are clearly made out when looking along the throat of the Esk from Bridge Street. Whitby Harbour was once an important maritime centre and dates to the Roman times. It the only natural harbour between the Tees and Humber estuaries.