Three words: come in March. The yearly Cheltenham Festival is the UK's top steeplechase event, attracting some 40,000 people to a race meet that culminates with the legendary Gold Cup. It's the key diary date in the jump racing calendar, offering four days of spills and thrills against the backdrop of the Cotswold Hills.
Horse racing doesn't get much better. If horses aren't your thing, try heading to the beautiful Promenade, a wide, almost Parisian style tree-lined boulevard that is home to some of the best shopping in town. If you're looking for upmarket fashion brands such as Reiss and Jigsaw, you'll find them here, and there are more shops and bars on neighbouring Regent Street. The latter is also home to the Everyman Theatre, whose spectacular period auditorium hosts everything from Shakespeare to panto.
Other nearby cultural attractions include The Wilson, Cheltenham's art gallery and museum. Permanent collections cover local history, the Arts and Crafts movement and much more, while temporary exhibitions range from painting to video art. For more superb shopping and entertainment, head south past the pretty Imperial Gardens to the Montpelier area. It's home to a host of fashionable hangouts, including bars, restaurants and boutiques.