32 times the royal family had fun at the races

The royal family and the races are a long-standing tradition dating back to the 19th century and it's one that is still followed today. Members of the royal family are often spotted at numerous races during the year, including Royal Ascot, the Cheltenham Festival and the Epsom Derby.

Attending these types of events and mingling with the public often allows us to catch a glimpse into the relaxed and more candid side of the most famous family in the world. Whether it's the late Queen cheering one of her beloved racehorses or the future monarchs sharing a joke during a trophy presentation, the races have given us plenty of amusing pictures that show the royal family having lots of fun.

So, we have brought together 32 of our favourite times the royal family had fun at the races.

32 times the royal family had fun at the races

The late Queen showing her support during the Epsom Derby

This famous picture of the late Queen shows her lifelong passion for horses and racing. Pictured in a rather eye-catching yellow outfit with a matching hat, she was clearly having the best time as she eagerly watched the races at the 1988 Epsom Derby with a programme in her hand. Prince and Princess Michael of Kent look just as excited and engaged by the events unfolding below. Spotted in a matching yellow outfit behind her sister, Princess Margaret is watching along too.

The King sharing a joke with a jockey

King Charles has given us plenty of funny moments throughout the years, all showcasing his playful sense of humour and ability to always be up for a joke. This sense of humour was no doubt in fine form in this picture taken from the 2023 Royal Ascot Gold Cup, as he is pictured sharing a rather funny joke with jockey Frankie Dettori while the Queen looks on smiling.

Two cousins having a right laugh

Here, the playfulness of two cousins is captured during Royal Ascot in 2015. Prince Harry and Zara Tindall seem as if engaged in a silly game as they lean into each other, with the Prince pulling a rather goofy look as he has his tongue out. Zara, on the other hand, has her hand in a gesture as if taking care to explain the rules of a game to her younger cousin… 

The royal sisters in the enclosure at Royal Ascot

Princess Margaret and the late Queen are photographed here enjoying some quality time with the Queen’s horse Restoration in the unsaddling enclosure at Royal Ascot in 1958. The sisters look happy as they pet the much-loved racehorse and chat to the trainer as excited onlookers watch events unfold.

The King and Queen sharing a laugh

This amusing snap of King Charles and Queen Camilla is just one of the many romantic moments the current monarchs have given us that show their love for one another. Spotted watching the Gold Cup race on the final day of the Cheltenham Races in 2006, the pair appear to be having a super fun time as they laugh while the race unfolds. The King appears as if covering his mouth to contain his laughter, while Queen Camilla smiles broadly. 

All smiles from Princess Anne

While the royal family attend races across the UK as part of a long-standing tradition, they also often take advantage of the event as a way to engage with the public and present the unified and friendly image of the royal family we have all come to know. Here is a cheery Princess Anne during the 2007 Cheltenham Festival as she happily chats with members of the public. Her relaxed expression and wide smile show that she was clearly having a lot of fun at the event. Just to the left of the Princess’ face, someone appears to have taken their hat off to show respect to a royal.

Princess Diana, the Duchess of York and the Queen showing off their fashion sense

Here is the late Princess Diana with Sarah Ferguson, Duchess of York and the Queen as they are snapped enjoying themselves (and perhaps shielding from the heat) at the 1987 Epsom Derby in their rather nostalgic 80s padded shoulder polka dot and fuschia pink formalwear. While the two are clearly enjoying a rather amusing conversation, the late Queen watches on in an equally nostalgic 80s yellow patterned blouse and wide-brimmed hat.

Enthusiasm from Queen Elizabeth

Here, the late Queen revels in Epsom Derby excitement as she watches on enthusiastically from the royal balcony in 2019. One of the many amusing moments of Queen Elizabeth at the races, she looks like she’s having a great time no doubt cheering on one of her many horses that were often entered into races. Her raised hand and open-mouthed expression make us think this must have been a rather tense moment! 

Princess Eugenie and Beatrice getting involved in the fun

Here, siblings Princess Eugenie and Beatrice appear to be having plenty of fun as they jump in the air and cheer on the late Queen’s horse Estimate during The Gold Cup on Ladies' Day at Royal Ascot in 2013. Princess Beatrice showed her edgier fashion sense as she wore a black dress embellished with jewels and a gold applique fascinator, while Princess Eugenie opted for shades of blue for her day at the races look that showed her timeless and elegant style.

Greeting the crowd at the Epsom Derby

Queen Elizabeth and her husband Prince Philip enjoy a day at the Epsom Derby races in 1989 from the Royal Box, a luxurious 50-guest private room that many have seen many royals come to enjoy the splendour of the Epsom races. The Queen showcases her fun race day style in a rather bright coral outfit, finished with a racing-related brooch and a hat with ribbon detailing. 

Post-war fun at Epsom Derby

In this snap taken from 1947, a young Queen and the Earl and Countess of Athlone are spotted greeting onlookers during the Epsom Derby in 1947. Their jovial facial expressions and rather luxurious outfits at this post-war racing event show the general happy nature of the entire nation as it emerged from World War Two.

A fashion moment from the Princess Royal

Showing her candid side at the 2024 Cheltenham Festival, here is a rather jolly Princess Anne attending ‘Style Wednesday’ (previously known as Ladies Day) at the Cheltenham Festival. She showcases some fun race day attire, wearing a herringbone patterned coat, a beige coloured hat and a pink-toned red lipstick that is both classic and fun.

Sharing sweets in the Royal Box

When we think of royals attending the races, we think of endless glasses of sparkling champagne and hors d’oeuvres aplenty. Bucking that trend and showing that they too sometimes just need a sugar fix, here is Zara Tindall and her friend Dolly Maude snacking on wine gums whilst watching the racing from the Royal Box at Epsom Racecourse in 2022. Two perfect examples of the outlandish hats synonymous with attending the racing, Zara opts for a flowery blue hat while her friend mixes bright colours and patterns with a yellow houndstooth fascinator with blue feathers. 

Having fun with 80s fashion

Princess Diana and Sarah Ferguson, Duchess of York remind us of the outlandish colour and pattern of fashion days gone by in this extremely nostalgic photo as they laugh and joke in rather eye-catching outfits at Royal Ascot in 1987. While the late Princess wore a yellow, blue, red and white flower dress with a turquoise hat, the Duchess wore an apple green wide-brimmed hat with a large bow and rather puffy-sleeved dress. 

The late Queen as a vision in blue

The Queen was a lover of all things equestrian, from riding horses during her annual summer holiday in Balmoral (she was often spotted going for a ride through the grounds) to her love of horse racing and keeping an eye on the results of the races. Here, that enjoyment for horses shines through as she smiles and jokes with a friend during the Epsom Derby in 2019. Her striking all-blue ensemble shows her love of a one-colour outfit, while her majestic blue ribboned hat is just one example of the many flamboyant and memorable hats she wore throughout her reign.

The thrill of the Epsom Derby

You can almost feel the infectious fun and adrenaline of the races as Prince Harry, Princess Eugenie and friend Jake Warren are pictured getting right into the action during the 2011 Epsom Derby. The open-mouthed expressions and what we can only assume to be Harry leaning forward for a closer look give us the sense that lots of fun and excitement were being shared on this day at the races. We wonder if they won! 

The monarchs keeping an eye on the action

This picture shows the late Queen and Prince enjoying their shared love of racing as they both eagerly watch a race through binoculars. While this photo is not outright funny, their perfectly symmetrical stance is quite amusing and shows the lovely relationship and many moments the Queen and Prince shared together throughout their lives and their long and happy marriage. Truly a sweet moment!

Arriving in style to Royal Ascot

Showing that you don’t always have to be driven around as a royal when attending important events, here is a young Queen Elizabeth and Princess Margaret on horses as they enter the Ascot Races in June 1969. While it is normal for royals to be driven around the grounds in a horse-drawn carriage, the royal ladies took it upon themselves to have some fun and ride their own transport to the event showing their spirited attitude when attending these iconic racing events. 

Prince Harry can't hide his excitement!

Prince Harry shows us he was most definitely having fun at the races as he avidly watches the racing from the royal box. With his hands in the air in anticipation of a win, he smiles as he stands next to a friend and an equally invested Prince Philip. We wonder what the result was!

Mother and Daughter together at Ascot

This sweet snap shows mother and daughter Carole Middleton and Catherine, Princess of Wales sharing a joke and having plenty of fun as they attend day one of Royal Ascot in 2017. Carole shows her excellent taste in fashion as she wears a powder blue sweetheart neckline dress and matching hat, tastefully paired with simple drop earrings and a pendant necklace. Her daughter, the Princess of Wales, also shows her timeless style as she wears a lace overlay white dress that is accessorised with pearl earrings and an embroidered fascinator.

Up close to the action at Royal Ascot, 1955

We can see the classic charm of Royal Ascot at its best as Princess Margaret and the late Queen are spotted engaged in a light-hearted conversation with trainer Noel Murless in the unsaddling enclosure. 

What makes this photo even more memorable is that it was taken just after the Queen’s horse Jardiniere won the King George V Stakes (no doubt the explanation for the Queen’s wide smile!). 

This triumphant photo of Princess Anne

Here is Princess Anne enjoying the thrill of the jumps at one of Britain's most prestigious racing events in 2014. Known for often turning up to the event unannounced according to People magazine, she clearly enjoyed her time as she was pictured overjoyed with a wide smile during one of the races! 

King Charles and Sophie, Countess of Wessex giggling at Royal Ascot

This heartwarming photo shows King Charles having a rather good laugh with his sister-in-law Sophie, Countess of Wessex at Royal Ascot in 2022. While it is obvious they are having a right laugh and clearly having fun at the races, we also have to take a moment to appreciate the Countess’ lovely purple-toned outfit worn for this race day - how elegant! 

Plenty of silliness between Prince William and friends

As we all know, going to events with friends often ends up with silly jokes and plenty of good times. That is also the case for Prince William, who was pictured playfully having his ear pulled by a friend as he concentrates on the racing on day four of the Cheltenham Festival. Rather bizarre (we know) but we think this captures the candid and rather goofy nature of the Prince that he has shown us many times over the years. 

A moment of Ascot days gone by from 1953

Queen Elizabeth II celebrated her coronation year with a triumphant appearance at Royal Ascot and appeared to be having a very good time as her horse Choirboy won the Royal Hunt Cup in June 1953. Looking equally as enthralled by the excitement of the races are the Queen Mother and Princess Marina, Duchess of Kent. 

The Duke and Duchess of Susex presenting an award

Prince Harry and Meghan Markle were frequent visitors to the Races before they stepped back from their royal duties in 2020. Here they are pictured having a fun time chatting with jockey Frankie Dettori as they presented him with the trophy on day one of Royal Ascot in 2018. 

From everyone’s rather open-mouthed expressions, we are assuming that a very fun (and no doubt cheeky) conversation was occurring. Meghan oozes classic Race Day style here as she wears a simple white dress accessorised with a black belt and a black and white hat with a bow attached to the front.

Zara Tindall & Co. show us why they love the Races

This funny snap shows Zara Tindall and her friend, Dolly Maude, getting extremely into the events unfolding on day one of Royal Ascot in 2015. Pictured from below as they stand in the royal box, Zara’s open mouth and her friends' excited facial expression and outstretched hands show they were both having a great time in matching lemon-yellow outfits. 

A tense moment for Queen Elizabeth

Here we have Queen Elizabeth enthusiastically watching the Gold Cup at the Cheltenham Festival in 2009. Her rather tense and animated expression reveals to us how the Queen was a lover of the races and really did get into her horse racing, especially when one of her horses was involved! 

Three royals showing us their timeless Race Day style

Here are Queen Elizabeth, Princess Margaret and the Queen Mother looking elegant at Epsom Racecourse in 1958. While they may look rather interested, they were clearly having so much fun that they decided to find a front-row view of the events as crowds of smartly dressed men in top hats gathered behind them. 

This photo also shows the timeless elegance of the royal family’s style choices, with all three women wearing feminine, neutral-coloured race day outfits that perfectly fit the theme of being outdoors and watching the races. From the late Queen’s layered frilly hat to Princess Margaret’s cool sunglasses, this picture captures the fun (and fashion!) of the races. 

This action shot of Queen Camilla at Ladies Day

This amusing snap shows the current Queen with a rather exaggerated and unfortunate look on her face as she was pictured attending the 2012 Cheltenham Festival. Clearly extremely invested in the racing unfolding below, Camilla eagerly holds binoculars in her hand with a look of shock and surprise. Other than her wildly amusing expression, we think the Queen once again showcased her eloquent style when attending race days, as she wears a teal lapelled coat and a pop of fun with a spotty blue and beige bowed blouse underneath. A fun fur wide-brimmed hat completes the look 

The Prince and Princess of Wales having a good laugh

The Prince and Princess of Wales were clearly having bundles of fun, judging by this lovely snap taken during Royal Ascot in 2022.  We think this photo is just one of the many numerous romantic moments that capture the connection and joy shared between our future monarchs. 

Zara and Queen Camilla feel the nerves at Cheltenham Festival

Zara Tindall and Queen Camilla show us the more stressful side of racing here as they eagerly (and nervously!) watch the Queen Mother Champion Steeple Chase horse race at the Cheltenham Festival in 2012. Camilla appears as if watching through her hands in nervousness while Zara simply can’t believe what’s going on and has her hand clasped over her mouth!