Cheltenham

The whole place is draped in honey-coloured Georgian terraces, wrought-iron balconies, and grand civic buildings that were designed to impress 18th-century aristocrats who came to "take the waters." That spa heritage is long gone, but the swagger remains.

Today the town runs on a relentless calendar of world-class festivals, from the thundering chaos of the National Hunt horse racing festival in March to the world's oldest literature festival every October. In between, there's jazz, science, music, cricket, and a homegrown indie music scene orbiting breweries like DEYA. Cheltenham also happens to be home to GCHQ — Britain's signals intelligence agency — whose distinctively circular headquarters (nicknamed "The Doughnut" by locals) sits just outside town and gives Cheltenham an odd dual identity: Regency elegance meets government surveillance.

The town is solidly middle-class and well-educated, with a large student population from the University of Gloucestershire. Expect good coffee, opinionated locals, and a genuine pride in the place that tips occasionally into self-satisfaction.

When you're out in a group, take turns buying drinks for everyone. Trying to pay only for yourself is considered antisocial.

Get in early and offer to buy the first round; you'll earn immediate goodwill.. Order at the bar, not at the table. Most traditional pubs don't do table service for drinks.

Head to the bar, make eye contact with the staff (don't wave or shout), and wait your turn patiently. Everyone knows who was there first — it's an invisible queue.. Tipping in pubs is optional.

You're not expected to tip bartenders. If the service has been good, the British way is to say 'and one for yourself?' — which means you're buying them a drink.

In restaurants, 10–15% is appreciated but check the bill first as service charges are increasingly added automatically.. Cheltenham Festival racegoers dress up. There's no official dress code, but the Gold Cup is essentially a fashion event as much as a racing one.

Smart attire is the norm; turning up in jeans to the Club Enclosure will get you noticed.. The 'Cheltenham roar' is real. When the tape goes up for the first race of the Festival, the crowd noise is genuinely extraordinary.

If you're going to the races, lean into it.. Gustav Holst was born here — Holst Birthplace Museum on Clarence Road is a genuinely underrated local treasure that residents are quietly proud of.. Last orders at pubs is usually called around 10:40–10:50pm, with closing at 11pm on weekdays.

Some bars in the Brewery Quarter stay open later on weekends. When you hear 'last orders,' act quickly.

It's the safest major town in Gloucestershire and sits well below the England-wide crime average overall. That said, it's not crime-free.

Bicycle theft runs notably above the national average, so always lock up properly. The town centre around pubs and the train station sees the usual concentration of late-night incidents — nothing unusual for a British market town, but worth being aware of after midnight on weekends. During the Cheltenham Festival in March, the town floods with tens of thousands of racegoers and the police run dedicated operations including plainclothes officers specifically watching for predatory behaviour in the night-time economy.

Stick to well-lit streets, look after your drink, and you'll be fine. Vehicle crime is another one to watch — don't leave valuables visible in parked cars. During festival periods, hotel prices spike dramatically and accommodation scams surface online.

Always book through official channels.

The town centre is compact, and most of what you'd want — the Promenade, Montpellier, the Suffolks, Imperial Gardens — is within a 20-minute walk of each other. Stagecoach runs buses around town every 15 minutes on popular routes, including a direct service between the train station, town centre, and the Racecourse.

The train station (called Cheltenham Spa, or "Lansdown" to locals) sits west of Montpellier and runs direct services on the Bristol–Birmingham main line. London Paddington takes around 2 hours 10 minutes; Bristol Temple Meads is roughly 40 minutes. CrossCountry, Great Western Railway, and others all serve the station.

There's no underground or tram, but that's fine for a town this size. During major events like the Racing Festival and the Jazz Festival, public transport frequency increases and parking in town changes — check ahead if driving. Two Park & Ride sites serve the town: Arle Court off the M5 (Junction 11) and Cheltenham Racecourse.

Taxis and Uber operate throughout. Hiring a bike is a good shout for exploring further — the Honeybourne Line is a flat, car-free trail running through town. For the Cotswolds villages beyond, a car or organised day tour is your best bet.