There are not many events that are worth getting up before 6am to day trip from London, but the Cheltenham Festival is one of them. Horse racing is one of the great British traditions and Cheltenham is the jewel in the crown. Although many people prefer the pomp and spectacle of Royal Ascot, the racing at Ascot is on the flat and Cheltenham is National Hunt racing i.e. hurdles and steeplechases (like the Grand National) and this is arguably much more interesting to watch.
Ascot is also very much about being seen in the right outfit – and the right hat – whereas Cheltenham is much less showy.

It’s a good thing that there’s no need to dress up as ridiculously as that for Cheltenham as not only is there almost always iffy weather and plenty of mud, getting there involved 3+ hours on a cramped coach after a ridiculously early start. I think we look pretty good under the circumstances…

Apart from what to wear to which race meeting, and what the difference between flat races and National Hunt is, I know absolutely nothing about horse racing and I would never normally place a bet on a horse. Part of the fun of attending a race meeting, however, is having a flutter – in the full expectation, of course, of losing the lot.
My approach to betting on a horse race is simple – I pick a horse with an amusing or appealing name, trying to avoid the favourite or any rank outsiders (although this time I couldn’t resist “WhatsWrongWithYou”). I also like to set my budgets and place all my bets for the entire meeting before getting down to the serious business of eating, drinking and socialising – and that means quite a while before the first race starts. In other words – don’t drink and bet!
This approach served me very well on my first trip to Cheltenham in 2017 when I bet and won on a horse called Special Tiara (who could resist that name?) and also won a couple of other bets, but last year I won nothing. This year wasn’t looking good either until the final race which was won by the irresistibly named Early Doors, meaning that I finished the day having lost considerably less of my £50 flutter budget than I expected.
Was it worth the 8+ hour round trip from home? It certainly was and I hope to be invited again next year (but perhaps I’ll travel by train instead of the rather grim coach).