Section 16 of The Trans-Pennine 100 enters the Wentworth Woodhouse estate passing the big house following the path through the deer park. 

Taking the Elsecar Skelter route in reverse the route enters Upper Haugh then takes a sharp left towards Hoober.

Passing The Needles Eye the route drops down the hill to find the checkpoint in Elsecar at the Parish Hall. 

• Wentworth Woodhouse is a Grade I listed country house in the village of Wentworth, in the Metropolitan Borough of Rotherham in South Yorkshire. It is currently owned by the Wentworth Woodhouse Preservation Trust. Considered to be the largest private residence in the United Kingdom (larger royal residences such as Buckingham Palace and Windsor Castle are not privately owned), it has an east front of 606 feet (185 m); the longest country house façade in Europe. The house has more than 300 rooms, although the precise number is unclear, with 250,000 square feet (23,000 m2) of floor space (124,600 square feet (11,580 m2) of living area). It covers an area of more than 2.5 acres (1.0 ha), and is surrounded by a 180-acre (73 ha) park, and an estate of 15,000 acres (6,100 ha).

  • The original Jacobean house was rebuilt by Thomas Watson-Wentworth, 1st Marquess of Rockingham (1693–1750), and vastly expanded by his son, the 2nd Marquess, who was twice Prime Minister, and who established Wentworth Woodhouse as a Whig center of influence. In the 18th century, the house was inherited by the Earls Fitzwilliam who owned it until 1979, when it passed to the heirs of the 8th and 10th Earls, its value having appreciated from the large quantities of coal discovered on the estate.

• Hoober Stand is a 30-metre-high (98 ft) tower and Grade II listed building on a ridge in Wentworth, South Yorkshire in northern England. It was designed by Henry Flitcroft for the Whig aristocrat Thomas Watson-Wentworth, Earl of Malton (later the 1st Marquess of Rockingham) to commemorate the quashing of the 1745 Jacobite rebellion. It lies close to his country seat Wentworth Woodhouse. Its site is approximately 157 metres (515 ft) above sea level and from the top there are long-distance views on a clear day. It is open to the public 2–5 pm on Sundays and bank holiday Mondays from the spring bank holiday weekend until the last Sunday in September. Hoober Stand is one of several follies in and around Wentworth Woodhouse park; the others include Needle's Eye and Keppel's Column.

• Needle's Eye is a 14-metre (46 ft) pyramid Grade II listed building which is situated in Wentworth, South Yorkshire in northern England. Needle's Eye is one of several follies in and around Wentworth Woodhouse Park, the others include Hoober Stand and Keppel's Column.

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