By Kaila Angello – Photographer Kaila Angello, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=6166454
There are few more interesting sports in the world than horse racing, with even the Triple Crown contests in the USA capturing the imaginations of those that wouldn’t typically watch the events.
The 2026 Kentucky Derby attracting a record 19.6 million, as Cherie DeVaux and Golden Tempo made history at Churchill Downs. However, the attention now switches to the Belmont Stakes and a crucial betting guide can be found here: twinspires.com/belmont-stakes/odds/
But, for long-time followers of the sport, they will typically look to attend events that are completely unlike anything else on the equine schedule. But, what are some of the strangest race days that are held across the world?
Palio di Siena
One of the most historic horse racing events that is staged annually comes in Italy, as the chaotic and passionate Palio di Siena is run twice per year.
Every July and August, international racing fans flock to Siena, as ten of the city’s 17 districts compete for a painted silk banner on horseback. The race is a pivotally important part of Sienese life and culture, with horses involved covering the distance across a mixture of turf and sand.
Unlike many lucrative races across the world, the Palio di Siena is uncommon due to the fact that a horse can win the race regardless of whether the jockey is aboard or not.
White Turf Skijoring
One of the craziest horse races anywhere in the world comes in the form of the White Turf Skijoring. This event in Switzerland is held on the frozen Lake St. Mortiz, with horses pulling skiers at speed of up to 60 km.
The race is the flagship event of the February White Turf Races, and it sees horses drag racers across the 2,700 meter track. It remains one of the most dangerous and unique events on the sporting calendar, and it has been a traditional event in Switzerland since its foundation in 1907.
Skiers face huge risks in the race, as they must display courage and strength to handle both the speed of the equine on the ice, and also deal with the kick-back of ice and snow that comes from the hooves of the horses.
Man versus Horse Marathon
In Wales, humans and horses go head to head in the pursuit of sporting success in the Man verses Horse Marathon. The race covers a total distance of 21 miles, with those involved competing across a range of road, mountainous, and trail terrains.
It is a huge date in the local calendar for residents in Llanwrtyd Wells every June, and it has been staged annually since 1980 following an overheard discussion in a local pub between two men.
One man argued that over a significant distance, a human could beat a horse, while the other argued that a horse would best a man. It would appear as though the latter was correct, with all but five editions of the race since the 1980s being won by a horse. However, Dewi Griffiths did become only the fifth human to win the race in 2025.
Mongol Derby
One of the most testing equine races on the international schedule is held annually through the Mongolian Steppe, with the Mongol Derby covering an extended distance of 1,000 kilometres.
That makes it the longest horse racing in the world. The course mirrors the distance covered by Genghis Khan in 1224, and it is a hugely significant event that attracts the attention from across the world. Back in 2016, 21 men and 23 women were involved in the race, seeing a total of 13 countries being represented.
In total, the race lasts for ten days, with riders spending around 14 hours per day in the saddle. However, due to sheer difficulty of the race for both riders and horses, it is common that only half of the field complete the circuit annually.
Chincoteague Pony Swim
One of the most unique horse racing events staged annually in the United States comes in the form of the Chincoteague Pony Swim. This century-old traditional event sees wild ponies swim across the Assateague Channel from Assateague Island to Chincoteague Island in Virginia.
The event is traditionally held in late July, and it is managed and organised by the Saltwater Cowboys to raise funds for the Chincoteague Volunteer Fire Company. It is typically held on the last Wednesday of July, and this year’s edition marks the event’s 101st anniversary. The event holds special historical importance to the local region, as it was chronicled in the book ‘Misty of Chincoteague’.
As well as serving a big fundraiser for the fire department, it gives vets the opportunity to check herds of wild ponies for illness, while also helping to maintain and control the population of equines in the region.