15 unmissable things to do in Cheltenham

Proud to be known as The Festival Town, there are 35+ annual festivals in Cheltenham which provide the perfect opportunity for shared experiences and life affirming moments with family and friends.

Enjoy a trailblazing mix of international stars, jazz icons and up and coming musicians at the Cheltenham Jazz Festival in the spring. Attend a meeting of the minds and hearts from the authors of some of your favourite page-turners at the Cheltenham Literature Festival in October. Or unwind and indulge with one of the many feel-good summer experiences Cheltenham has to offer including the Food and Drink Festival and Wychwood Festival.

A spa resort town wouldn’t be complete without a racecourse. Cheltenham Racecourse is the jewel in jump racing crown. Playing host to some of the best jumping action in the world from 350 spectacular acres in the lee of the beautiful Cotswold Hills.

Whether you're here on a crisp bright October day for The Showcase, a balmy evening in May for Race Night or joining the crowds for the biggest jump racing event in the UK, The Cheltenham Festival, in March, you'll feel the unmistakeable Cheltenham magic. The racing, the setting, the tradition and history, and the shared sense of enjoyment all combine to give race goers an experience they’ll never forget.  

A visit from King George III to Cheltenham’s original mineralised spring in 1788 secured Cheltenham's position as a spa town and became a catalyst for its transformation into a sought-after destination for the wealthy.

These days Cheltenham’s spas and wellness centres are a major draw for visitors from all over the world. So, why not treat yourself to some self-love and care with a spa experience at the likes of C-side, Ellenborough Park, or the Greenway Hotel and Spa.

Images - Pittville Pump Room (left), Cheltenham Town FC (top), GWSR steam railway (bottom).

Cheltenham’s own professional association Cheltenham Football Club hold frequent matches at the Johnny-Rocks stadium on Whaddon Road with other League One teams. So, grab your jersey and enjoy a thrilling atmosphere unlike any other. 

Known as ‘The Friendly Line in the Cotswolds’ GWSR offers a unique opportunity to sample the glory of steam train travel from 50 years ago. With a 29 mile round trip from Cheltenham Racecourse train station through the picturesque Cotswold countryside, past hamlets and villages, you’ll be treated to panoramic views of the Malverns, the Vale of Evesham and Wales.  

Due to the size, number and frequency of the Regency style buildings in Cheltenham, it has been named 'Britain's most complete Regency Town'.

From the iconic Pittville Pump Room which stands grandly at the head of a sweeping lawn in Pittville Park, to the shopping district of Montpellier with the gorgeous fluted columns and Caryatids, there are plenty of Regency sights to soak in and enjoy.

Why not take in the history of the town and discover the Cheltenham of Jane Austen, Lord Byron and the Duke of Wellington with a guided walking tour. Or enjoy the Regency splendour at your own pace, on two wheels or on foot with our self-guided Cheltenham tour and public art trail.   

Images - Sri Lankan street food at The Coconut Tree (left), crowds at 2000Trees (bottom), performance of Hairsprary at Everyman Theatre (bottom).

The Everyman Theatre in Cheltenham is Gloucestershire's theatre - and has been serving the county (and beyond) since 1891. The Everyman boasts a packed calendar of brilliant shows and performances year-round.

The main auditorium is an architectural masterpiece designed by Frank Matcham that has inspired generations of performers. So, whether you visit the Everyman to see ballet, opera, drama, dance, comedy, music events or their traditional family pantomime you’ll enjoy it all in majesty.

The Everyman isn’t the only Cheltenham live performance venue. Cheltenham Town Hall has a year-round supply of electrifying acts to brighten up a dreary evening. With a mix of household comedy and musical names including Ed Gamble, Sara Pascoe and Fisherman's Friends,  the Town Hall is the perfect place for a memorable evening with family and friends. 

There are also packed year-round programmes to enjoy at the more intimate Bacon Theatre and Cheltenham Playhouse Theatre.

See our guide featuring concerts, shows, comedy acts and more here – Cheltenham Live Performances.

Named Britain’s coolest festival by Kerrang! Magazine, 2000trees is a 15,000 capacity music festival held in July and set in the rolling Cotswold Hills. Revel in a friendly, intimate atmosphere, with 130 of the best bands that the world has to offer, plus amazing food and locally produced ciders, ales & lagers.

Cheltenham is fortunate to have many award-winning restaurants peppered throughout the town. Luxuriate in the fine dining of Michelin Star & 4 AA rosettes restaurant Le Champignon Sauvage or Cheltenham's newest Michelin star restaurant - Lumiere. Enjoy the warmth of Sri Lankan hospitality & cuisine at the Coconut Tree in St Paul’s. Or travel to the colourful streets of Tokyo at KIBOU, an award-winning Japanese hot kitchen and bar in the heart of the town centre. 

The town is also home to many incredible independent restaurants, all offering exceptionally good service and delicious food you simply won't find anywhere else. Enjoy fabulous sustainable caught seafood at Purslane. 

For more dining inspiration check out – Cheltenham restaurants, Cheltenham bars, independent places to eat in Cheltenham.

Images - Sushi at KIBOU (top), walk on Leckhampton Hill (bottom), cocktail waiter (right).

Cheltenham has a plethora of brilliant places to drink and be merry in the town. Check out the many pubs on Bath Road, such as the Exmouth Arms and neighbouring Bath Road Beers for home-style cooking, local brews and sun-soaked beer gardens. 

Visit The Brewery Quarter just off the High Street for social darts and sips at the newly opened Flight Club, as well as upmarket cocktails and clever concoctions at The Botanist and The Alchemist.

Travel slightly further afield and discover unique venues you won’t find anywhere else. Soak up the atmosphere at Dunkertons Cider in Dowdeswell Park; across the road you’ll find Sibling Distillery and Battledown Brewery and just behind Cheltenham Spa train station you can explore Cheltenham's local brewery, DEYA Brewing Company, and try the beer for yourself in the DEYA Taproom.

For more evening inspiration check out - Cheltenham pubs & bars, Cheltenham beer gardens, Cheltenham wine bars and Cheltenham cocktail bars.

Sitting in the middle of a valley, Cheltenham is surrounded by beautiful open spaces to spend many a leisurely day roaming. Visit the Devil’s Chimney atop Leckhampton Hill, take the dog out and explore the rich wildlife of Crickley Hill or enjoy a sunset overlooking the Cheltenham Racecourse at the top of Cleeve Hill.  

Cheltenham is also lucky enough to have some stunning nature reserves and Sites of Special Scientific Interest (SSSI) which make the most of our stunning Cotswold location. Griffiths Avenue Nature Reserve includes two meadows of wildflowers which support fifteen species of butterfly along with several large mammals such as badgers and foxes. Meanwhile, the Wildfowl and Wetland Trust is just a short drive from Cheltenham and comprises more than 800 hectares of specialist habitats. 

Cheltenham, and in particular Cheltenham’s eclectric art quarter of Montpellier, boasts several public art galleries and private collector galleries where you can enjoy a pleasurable few hours. 

The beautiful regency setting of Montpellier, just a short walk from the Cheltenham Promenade, provides the backdrop to six independent and distinct art galleries. With its history, architecture, tree lined streets and a picturesque green space, Montpellier’s charming ‘outdoors’ sets up any visitor for the delights found ‘indoors’ within its galleries, all of which are within 200 metres of each other. Discover more - Montpellier Art Galleries Cheltenham.

Cheltenham has long been associated with the arts, and Montpellier is the natural home to the literature, jazz and food festivals, with the year-round representation from its resident galleries. The Montpellier art experience is not just about the paintings on a wall or the sculptures on their plinths, beautiful as they are. The galleries dovetail perfectly with the specialist shops, bars, restaurants, coffeehouses located there, to offer a unique and worthwhile visit that can last the whole day.

If you prefer the raucous and rough-edged quality of street art to that found in a gallery then Cheltenham has got you covered here too. 

Since 2017 the Cheltenham Paint Festival has been brightening up the streets of the Regency Town with incredible street art by renowned urban artists such as Inkie, Dank and Fabio Petani.  

One of the best things about the Cheltenham Paint Festival is that many of the large scale / full wall art murals remain permanent fixtures so they can be enjoyed year-round. Download the informative app, or a map, from the Paint Festival website and take in the incredible sights of the 8k street art route whenever you feel the urge!  

Cheltenham’s two main museums are the perfect places for arts and culture lovers to explore local history.

The Holst Victorian House pays homage to Gustav Holst in the house where he was born and raised, preserving the Regency facade and decor of the building, as well as the pianoforte used to compose The Planets piece and many other artefacts too. 

The Wilson Art Gallery and Museum has been significantly refurbished to re-cement the centre as Cheltenham’s leading cultural hub. The new space includes a vibrant arts café, the Sir Charles Irving Community Art Gallery, and new artists’ studios.

Images - Childrens session at Holst Victorian House (left), Art Gallery in Imperial Gardens (top), street art from the Cheltenham Paint Festival (bottom).