Things To Do in Cheltenham: A Guide to the 6 Top Attractions

Affluent, elegant and easy to explore on foot, Cheltenham in Gloucestershire is justly renowned for its sublime Regency terraces, crescents and mansions, expansive public parks and year-round schedule of festivals. It began life more than a millennium ago as a medieval village, but its fortunes were changed forever with the discovery of mineral springs in 1716. Cheltenham soon morphed into one of the most famous health spas in England, over the years attracting royal visitors like King George III and Queen Victoria, along with all manner of 18th-century A-list celebrities – including the Duke of Wellington and Jane Austen – to sample the life-giving properties of its waters. You can still sip from the springs today at a number of contemporary spas, and the town, along with its surviving Regency architecture, remains a wonderful place to explore, relax and regroup.

Although it’s tempting to cram all the attractions and sights of Cheltenham into your stay, the town is historically all about relaxing, so take your time and absorb its beauty. Here are six things to do in Cheltenham that reflect its Regency past, yet catch the essence of its thoroughly 21st-century zeitgeist.

Discovering the handsome district of Montpellier – home to many graceful Regency buildings and manicured parks – is one of the first things to do in Cheltenham. Its story is inextricably entwined with the development of a new spa in 1801, which saw the construction of rows of multi-storey townhouses with smooth, symmetrical façades, wrought-iron balconies and panelled doors. Alongside this domestic architecture, several public buildings sprang up, including Montpellier Arcade, believed to be the world’s first shopping centre, and Montpellier Walk, with its shop fronts supported by The Caryatids – 32 gleaming white sculptures fashioned in Neoclassical style. The colonnaded Rotunda is another masterpiece from this era, built as a pump room and topped with a dome – this storied edifice has done time as a bank and restaurant since the demise of Cheltenham as a spa in the 1830s.
 

The Montpellier District may be Grade I listed and fiercely protected, but it’s kept up with the times. Today its ornate streets house contemporary boutiques and artisan jewellers as well as a myriad of pubs, cafés and fine-dining restaurants.

• Cheltenham GL50 2DY
• Open 24/7

To use its full name, the superb Wilson – Cheltenham Art Gallery and Museum is Gloucestershire’s standout museum. Making time to see the exceptional Arts and Crafts collection – as inspired and led by Cotswolds-based William Morris – should be one of the things you definitely do in Cheltenham. Spanning the 1880s to 1940s, pieces are displayed in rotation but you can expect to see exquisite Liberty shawls, filigree silver work brooches by CR Ashbee from Chipping Campden and finely carved furniture from Ernest Gimson, who also had a studio in the Cotswolds.
 

Other permanent exhibitions showcase local explorer Edward A. Wilson and his adventures with Scott of the Antarctic, and a fascinating glimpse into the social history of Cheltenham. Fans of Old Master paintings will find much to enjoy in the significant 17th-century Dutch art on display, and The Wilson also hosts an ever-changing programme of thought-provoking exhibitions.

• 51 Clarence St, Cheltenham GL50 3JT
• Open Tue–Sat 10am–5pm; Sun 10am–4pm
• Admission free with a suggested donation of £3

All sweeping lawns, mature trees and lakes, Pittville is the largest of Cheltenham’s ornamental green lungs. Flanked by regal Regency mansions, its shaded paths lead to lots of family-friendly amenities, from play areas and aviaries to tennis courts, a BMX park, mini-golf course and a boating pond. It’s a splendid place to rest up and regroup after a session of sightseeing, but if the weather’s not playing ball, there are a couple of cafés too.
 

One of the crown jewels of Cheltenham’s Regency heritage is found in Pittville Park. Adorned with Ionic columns and statues of Ancient Greek gods, Pittville Pump Room is evocative of a bygone age, when the crowds surged in to take the (slightly unpleasant) waters, linger over afternoon tea and flirt at formal balls by night. Like so many other fine Cheltenham landmarks, it has had a contemporary makeover and today the former ballroom serves as a rather grand events space where the occasional pop-up market is held. A free self-guided walking trail takes this beautiful building back to the grandeur of its 18th-century heyday.

• Prestbury, Cheltenham GL50 4SH
• Open 24/7
• Free admission for 2 hours

Overlooked by the landmark Cleeve Hill, Cheltenham Racecourse is the premier National Hunt (jump racing) course in the UK, with around 400,000 people attending events every year. It’s such a beacon to racegoers that if you visit the town in mid-March, expect it to be overflowing with life in anticipation of the annual Cheltenham Festival, a world-famous four-day bonanza bringing in international racing pilgrims from across the globe. One of the best things to do in Cheltenham, the festival culminates with the prestigious Gold Cup and a mighty pot of prize money for the winning jockeys, owners and trainers. The jump season calendar runs from October to May; during that time eight race meetings provide sixteen days of quality racing.
 

But it’s not all about the horses here; there’s a shopping village on most race days, and world-class seasonal cuisine served in a variety of gourmet restaurants. Throughout the year the course managers also lend out its 150 hectares of rolling Cotswold countryside to big-name rock and classical concerts, art exhibitions and the family-friendly Wychwood music, comedy and literature festival in early June.

• Evesham Rd, Cheltenham GL50 4SH
• Tickets start at £12
  

Attending festivals is another very popular thing to do in Cheltenham, just as it is in the Scottish capital, Edinburgh. The year kicks off with horse racing’s money-spinning Gold Cup in March, and as the months progress, a diary-busting cavalcade of literary, musical and foodie celebrations beckon thousands of visitors into town. Here’s the cream of the crop.

• Cheltenham Craft Fair: Craft workshops and free activities for children.

• Fresh: Art Fair: The chance to snap up works from famous names like Banksy and David Hockney at bargain prices.

• Cheltenham Jazz Festival: Always featuring a line up of the biggest and best musicians in jazz.
• Cheltenham Festival of Performing Arts: First held in 1926, this is the granddaddy of Cheltenham festivals and has lots of involvement from local schools.
• Pride in Cheltenham: Inclusive activities for the LGBTQ+ community plus all ages and all comers.
• Cotswold Festival of Steam: Vintage steam engines put in appearances on the Gloucestershire Warwickshire Steam Railway.

• Cheltenham Science Festival: A gathering of the UK’s science boffins to debate current hot topics like ageing and climate change.
• Cheltenham Food and Drink Festival: Live music, free wine tastings, artisan food producers and presentations from celebrity chefs.

• Cheltenham Music Festival: Performances by leading international artists and emerging talent over 8 days.
• Cheltenham Cricket Festival: A few days of top-quality cricket in the gorgeous grounds of Cheltenham College.
• Cheltenham 7s Festival´: A curious combination of rugby, netball and dodgeball with solo artists, bands and DJs.

• Cheltenham International Film Festival: A salute to world cinema with celeb guests, global hits and a focus on a different country every year.

• Cheltenham Literature Festival: The world’s longest-running literature festival, with events held in theatres and venues around town.

If you’re looking for things to do around Cheltenham, there’s a good reason why the town is called the “cultural capital of the Cotswolds”; lying on the fringes of this idyllic National Landscape, it draws in visitors and local residents alike for its shopping, race days and roster of festivals. It’s a two-way journey, however, as Cheltenham is the perfect springboard for day trips to delightful, honey-hued hamlets, pretty market towns and visitor attractions like Chedworth Roman Villa in the undulating Cotswolds countryside.
 

Follow the driving loops collectively known as the Romantic Road, which start in Cheltenham itself, with itineraries taking in stunning Stow-on-the-Wold and Bourton-on-the-Water, as well as lesser-known treasures such as the half-timbered cottages in Northleach. If you fancy leaving the car behind, go green and hop aboard the Gloucestershire Warwickshire Steam Railway to explore the region from its six stations, including Broadway and Winchcombe.

The university city of Oxford is also a popular day trip from Cheltenham, as it's only an hour's drive away. With so many amazing things to do in and around Cheltenham, plan your visit today!