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Among the many valuable items on the block, the November 30 Bonhams Bond Street Auction will have two special motorcycles up for grabs: a 1929 Brough Superior 986cc SS100 Alpine Grand Sports and a 1950 Vincent 998cc Series C Black Shadow.

Estimated at £270,000-320,000, the Alpine Grand Sports ($435,000 – $517,000) is named after the Alpine Trial, a famously grueling reliability run started in 1910. Taking in vast mountain peaks, chilling temperatures, and the twists and turns of Austria, Croatia, Slovenia and the infamous Stelvio Pass, it was a great test of endurance and skill – and not just for four-wheels.

George Brough – founder of the motorcycle marque – undertook the Trial in 1925 on an SS100, resulting in the award of six cups, including one for ‘Best Performance.’ The design of the Brough Superior Alpine Grand Sports took inspiration from its founder’s achievement, and was introduced to the market in 1925 for the 1926 season with a lower compression ratio (making it suitable for touring), a small fly-screen and a pair of tool boxes as standard – perfect for thundering through the Alps.

Ben Walker, Director for Bonhams Motorcycle Department said: “Brough Superior is a legendary marque in the motorcycle world. Coined the ‘Rolls-Royce’ of motorcycles, their distinguished status is well earned, with Brough products of the highest quality and engineering excellence, admired by all and highly sought-after – almost 100 years after the Haydn Road Works first opened their doors.

“The most charismatic of the marque’s stable is unquestionably the SS100 and we are delighted to be offering the model in its ultimate guise, a Vintage example in Alpine Grand Sports specification, boasting matching registration, frame and engine numbers – designed to honor the legendary Alpine Trial – the most arduous motoring test of its time.”

1950 Vincent 998cc Black Shadow Series C - 3_feature

With a top speed of 125mph, the incredibly swift Black Shadow was faster than any vehicle of the time. It’s this peerless performance that made it an icon of the 1950s and one of the most desirable of all machines today.

In the half-century since production ceased the esteem in which this iconic motorcycle is held has only increased, fueling the demand among discerning collectors for fine examples of the marque, such as that offered at Bonhams sale, which retains matching registration, frame and engine numbers, carrying an estimate of £70,000-90,000 ($112,000 – $145,000).

The duo of legendary motorcycles will be on display at Bonhams London to Brighton Run sale preview held at 101 New Bond Street this week (30th – 31st October), and will also take part in the National Motorcycle Museum’s 30th Anniversary celebrations this Saturday, 1st November.

Bonhams Bond Street Sale takes place at Bonhams London headquarters on 30th November 2014.