Two of the greatest events on the British sporting and social calendar. Both iconic. Both unmissable. But Royal Ascot and the Cheltenham Festival could not be more different. One is a celebration of flat racing, fashion, and royal pageantry under a summer sky. The other is four days of raw, edge-of-your-seat National Hunt drama in the heart of the Cotswolds. Choosing between them often comes down to the kind of experience you are looking for, and with ICON by Engage offering exclusive hospitality at both venues, you do not necessarily have to choose at all.

Here is our full guide to help you decide which event is right for you in 2026.

The Basics: What Are They?

Royal Ascot

Royal Ascot is the most prestigious flat racing festival in the world. Held every June at Ascot Racecourse in Berkshire, it attracts the finest thoroughbreds from across the globe, competing for a total prize fund of over £10.65 million across 35 races. Eight of those races carry Group 1 status, the highest level in the sport.

2026 dates: Tuesday 16 June to Saturday 20 June

The meeting is attended by the Royal Family every day, with King Charles III and Queen Camilla leading the famous Royal Procession along the Straight Mile at 2pm before racing begins at 2:30pm.

Cheltenham Festival

Cheltenham is the pinnacle of National Hunt racing, or jump racing. Held each March at Cheltenham Racecourse in Gloucestershire, the four-day festival features 28 races across some of the most demanding fences and hurdles in the sport. It draws around 250,000 racegoers and is famously described as the World Cup of jumps racing.

2026 dates: Tuesday 10 March to Friday 13 March

The meeting is particularly popular with Irish racing fans, and the British-Irish rivalry, celebrated through the Prestbury Cup competition, adds an extra layer of excitement to every race.

The Atmosphere

Royal Ascot: Glamour

Royal Ascot is as much a social occasion as a sporting one. The atmosphere is refined and celebratory. Champagne flows, fascinators bob, and racegoers dress immaculately across all five days. There is a genuine sense of occasion from the moment the gates open at 10:30am.

Each afternoon builds towards the Royal Procession at 2pm, when the Royal Family arrive in horse-drawn carriages, a tradition that dates back to 1825. Once racing begins, the crowd’s energy builds steadily through the afternoon. The roar as horses approach the finish line on the famous Straight Mile is something you will not forget.

Ladies Day on Thursday is especially spectacular. It is the day the Gold Cup is run, and fashion takes centre stage alongside some of the finest staying horses in Europe.

Cheltenham Festival: Raw Passion and the Famous Roar

Cheltenham is something else entirely. The atmosphere is described by many racegoers as the greatest in sport. The famous “Cheltenham roar” that greets the starter’s flag for the first race each day is a sound that sends shivers down the spine, even on a repeat visit.

The crowd is deeply knowledgeable and passionate. With around 65,000 people packed into Prestbury Park each day, the energy is electric from the moment the gates open. When the leading fancies for the big races parade in the ring, the buzz is palpable. And when a race unfolds up the famous Cheltenham hill, the noise is deafening.

St Patrick’s Thursday takes the atmosphere to another level. The Irish contingent floods the stands and the Guinness Village, and the sense of camaraderie between British and Irish racegoers, fierce rivals on the track but great friends off it, is unique in sport.

In summary: Royal Ascot is sophisticated and celebratory. Cheltenham is passionate, electric, and unfiltered. Both are extraordinary.

The Racing

Royal Ascot: Flat Racing at its Finest

Royal Ascot features some of the most valuable and prestigious flat races anywhere in the world. The 2026 meeting includes eight Group 1 races, with two of them, the Prince of Wales’s Stakes on Wednesday and the Queen Elizabeth II Jubilee Stakes on Saturday, each worth £1 million in prize money.

Key races to look forward to in 2026:

• Platinum Jubilee Stakes (Saturday): A £1 million sprint finale that draws the fastest horses from around the globe.
• Queen Anne Stakes (Tuesday): The opening race of the meeting and one of the most competitive miles in the calendar. Worth £750,000.
• St James’s Palace Stakes (Tuesday): A Group 1 for the best three-year-old milers. Won in 2025 by the brilliant Field Of Gold in one of the performances of the year.
• Prince of Wales’s Stakes (Wednesday): The richest race of the week at £1 million, attracting the world’s best middle-distance horses.
• Ascot Gold Cup (Thursday, Ladies Day): The oldest race at Royal Ascot, dating back to 1807. A supreme test of stamina over two and a half miles. Trawlerman set a course record when winning in 2025.

Cheltenham Festival: National Hunt Drama

If flat racing is about elegance and speed, National Hunt is about courage and stamina. Cheltenham tests horses over fences and hurdles on a track that rises dramatically at the finish. The famous Cheltenham hill has broken many a favourite in the final strides.

The four days each have their own identity, each headlined by a championship race:

• Gold Cup Day (Friday): The crescendo. The Cheltenham Gold Cup is the greatest race in jump racing, run over three miles and two and a half furlongs. It is the race that defines careers and creates legends.
• Champion Day (Tuesday): Headlined by the Champion Hurdle, the championship for the best hurdlers in training. Worth £450,000.
• Ladies Day / Style Wednesday (Wednesday): Features the Queen Mother Champion Chase, one of the fastest and most thrilling two-mile chases in the sport.
• St Patrick’s Thursday: The Stayers’ Hurdle and, from 2026, the Mares’ Hurdle, which has been moved to this day for greater prominence.

In summary: Royal Ascot offers speed, class, and global star power. Cheltenham offers drama, guts, and moments that live forever.

The Dress Code

Royal Ascot: Formal and Fashion-Forward

Royal Ascot has one of the most famous dress codes in sport, with specific requirements that vary by enclosure.

In the Queen Anne Enclosure, gentlemen must wear a suit with a collared shirt and tie, while ladies are required to wear formal daywear with a hat or headpiece. The Royal Enclosure has even stricter requirements.

Ascot is a genuine fashion event. Millinery is taken seriously, with many guests commissioning bespoke hats for the occasion. The dress code is enforced at the gate, so preparation is essential.

Cheltenham Festival: Country-Smart, Practically Stylish

Cheltenham does not enforce a strict dress code, but there are strong unwritten expectations, particularly in the Club Enclosure and hospitality areas. Gentlemen are advised to wear a jacket and tie or suit, while ladies typically opt for elegant, weather-appropriate outfits.

Given that the Festival takes place in March, practicality matters. Tweed is a popular and entirely appropriate choice for both men and women. Sturdy boots are sensible, given the ground conditions. The aesthetic is country-smart rather than urban-formal, and there is no shame in layering up when the Cotswold wind picks up.

The dress code for ICON by Engage at Cheltenham is: smart day wear for ladies (hats optional), and jacket and tie or suit for gentlemen.

In summary: Royal Ascot demands the full formal wardrobe. Cheltenham rewards thoughtful, weather-ready dressing.

Corporate Hospitality: What Each Offers

Both events are outstanding for entertaining clients, rewarding teams, or simply marking a milestone in style. But they offer different things.

Royal Ascot Hospitality

Royal Ascot is polished, refined, and prestigious. The setting, the Royal Family’s presence, and the fashion make it an immediately impressive environment for guest entertainment. It is an event that virtually everyone has heard of, regardless of their interest in racing. Arriving for a day at Royal Ascot, particularly with premium hospitality, makes a statement.

It works exceptionally well for:

• Senior client entertainment and VIP relationship-building
• Team rewards that feel genuinely exclusive
• Occasions where presentation and prestige matter
• Guests who will enjoy the fashion, the pageantry, and the social scene as much as the racing

Cheltenham Festival Hospitality

Cheltenham is energetic, passionate, and genuinely thrilling. Guests do not need to know anything about racing to feel the electricity in the air. The atmosphere carries everyone along, and a winning bet on a big race creates the kind of shared moment that brings groups together instantly.

It works exceptionally well for:

• Racing enthusiasts who have always wanted to attend the Festival in style
• Entertaining guests who love sport and want to feel close to the action
• Group occasions where energy and fun are the priority
• Those who want to experience one of Britain’s great sporting traditions

ICON by Engage: Exclusive Hospitality at Both Venues

At Engage, we offer our flagship ICON facility at both Royal Ascot and Cheltenham Festival, giving you an unmatched experience at each of Britain’s greatest race meetings.

ICON at Royal Ascot

Our ICON facility at Royal Ascot places you at the heart of one of the most famous sporting spectacles in the world. You will enjoy premium hospitality with views of the racing, exceptional dining, and access to an experience that matches the grandeur of the occasion.

Royal Ascot 2026 runs from Tuesday 16 June to Saturday 20 June. Our packages are available across the week, including for Ladies Day on Thursday and the dramatic finale on Saturday.

Find out more about ICON at Royal Ascot

ICON at Cheltenham Festival

Our ICON by Engage suite at Cheltenham is a stunning glass-fronted hospitality space with a private balcony offering panoramic views of the iconic racecourse. From this vantage point, you can see the final furlong, the finishing straight and the Cleeve Hills as a backdrop. You will feel every moment of the racing as the horses thunder past just metres away.

Guests enjoy gourmet dining, free-flowing Champagne, and exclusive access to racing legends throughout the day. Our suite is located in the Long Run Boxes on Level 2, accessible via the North Entrance, and offers some of the finest viewing anywhere at Cheltenham Racecourse.

The 2027 Cheltenham Festival hospitality packages are now available to book.

Find out more about ICON at Cheltenham Festival

So Which Should You Choose?

If you want elegance, summer sunshine, Royal pageantry, and the finest thoroughbreds in the world competing on one of racing’s great stages, Royal Ascot is your event.

If you want raw sporting passion, the roar of 65,000 fans, Irish rivalry, and four days of jump racing drama that will have you on your feet from first race to last, book Cheltenham.

And if you want both? We can make that happen too. With ICON by Engage available at both events, you could start your racing year with the Cheltenham Festival in March and return in June for Royal Ascot. Two completely different experiences. Both unforgettable.

Get in touch with the Engage team to discuss your options for 2026 and 2027.

Frequently Asked Questions

When is Royal Ascot 2026?

Royal Ascot 2026 takes place from Tuesday 16 June to Saturday 20 June at Ascot Racecourse, Berkshire.

When is the Cheltenham Festival 2026?

The 2026 Cheltenham Festival ran from Tuesday 10 March to Friday 13 March. The 2027 Festival is expected to take place in March 2027.

What is the difference between Royal Ascot and Cheltenham?

Royal Ascot is a flat racing festival held in summer, known for its formal dress code, Royal Family attendance, and glamorous atmosphere. Cheltenham Festival is a jump racing festival held in March, famous for its passionate atmosphere, Irish rivalry, and legendary races such as the Gold Cup.

What is ICON by Engage?

ICON by Engage is our flagship premium hospitality facility, available at both Royal Ascot and Cheltenham Festival. Guests enjoy gourmet dining, Champagne, exclusive views of the racing, and access to racing legends.

Do I need to know about horse racing to enjoy Royal Ascot or Cheltenham?

Not at all. Both events are as much about the experience, the atmosphere, and the occasion as the racing itself. First-time racegoers are made extremely welcome, and our hospitality team will help you get the most from your day.