Epsom, United Kingdom

Epsom is hardly the glamorous, vibrant city its Derby may suggest. With over 100,000 spectators cramming the free-admission Hill on race days, the crowds bring a festival atmosphere, but also a persistent headache of bureaucracy and logistics. The race's rich history dating back to 1780 is undeniable, though the modern event has struggled to maintain high attendance. For those drawn to the pomp and pageantry of British traditions, Epsom may hold appeal, but the realities of navigating its congestion and red tape make it a poor choice for most.