15 unmissable things to do in Cheltenham

There is so much to do in the Regency town of Cheltenham. This guide has been written to help visitors (and locals) make the most of their time here. Featuring the thriving arts and festival scene, award-winning bars and restaurants and spectacular Cotswold scenery. Here are our top 15 things to do in Cheltenham…

Images - Jazz performer at the Cheltenham Jazz Festival (left), Parade Ring at Cheltenham Racecourse (top), spa at Ellenborough Park (bottom)

Refresh your mind, body and soul at a fantastic festival

Proud to be known as The Festival Town, there are 30+ 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.

For more inspiration check out the 30+ cultural festivals and major sports events here – Cheltenham Festivals

Experience a day at the races

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.  

Unwind with a luxurious spa experience

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)

Cheer on the team at Cheltenham FC

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. 

Enjoy a picturesque trip on a steam railway 

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.  

Take in the Regency splendour

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, and on two wheels, with the  Regency Cheltenham Cycle Trail or on foot with our self-guided Cheltenham tour.  

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

Experience a show at the Everyman Theatre

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, with highlights for 2022 including Agatha Christies The Mousetrap, Titanic The Musical and The Two Popes.    

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.

Non-stop laughs at Cheltenham Town Hall, Playhouse Theatre & Bacon Theatre

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 names including Ed Gamble, Sara Pascoe and 2022's Britain's Got Talent winner Axel Blake, as well as feisty up and comers duking it out at the Cheltenham Comedy Festival in April. The Town Hall is the perfect place to laugh your troubles away.  

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

Enjoy intimate music festival vibes at 2000trees

Named Britain’s coolest festival by Kerrang! Magazine in 2018, 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 such as Jimmy Eat World and Idles, plus amazing food and locally produced ciders, ales & lagers.

Indulge at an award-winning restaurant 

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. 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 cheese fondue at Domaine 16 or fabulous sustainable caught seafood at Purslane. 

For more dining inspiration check out – Cheltenham Restaurants, Cheltenham Bars, Great Taste of Cheltenham, Independent Restaurants & Cafes Cheltenham

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

Enjoy a cheeky tipple at the many bars and breweries 

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.

Stretch your legs during an unforgettable countryside walk

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. 

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

Ignite your creativity at an art gallery

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 mooch for the afternoon. 

The Gardens Gallery in Montpellier Gardens is a gorgeous space that regularly features unique original collections not seen anywhere else. Nearby you’ll find The Paragon Gallery, Park Gallery and the Gloucestershire Guild of Craftsmen all stocked full with unique crafts and art. Meanwhile, The Parabola Arts Centre is attached to the Cheltenham Ladies' College and is often used as a festival venue, as well as having a small number of public exhibits annually. 

The Hardwick Gallery features a dynamic calendar of public exhibitions, talks and workshops, while Spring Cheltenham is the newest addition to the Cheltenham art scene, established by Cheltenham based artist Conrad P Clarke in 2021.

Explore the blossoming street art scene

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 a map from the Paint Festival website and take in the incredible sights of the 8k street art route whenever you feel the urge!   

Travel through time and discover Cheltenham’s fascinating history

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

The Holst Birthplace Museum 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. 

Meanwhile, The Wilson Art Gallery and Museum has recently seen significant refurbishments to re-cement the centre as Cheltenham’s leading cultural hub. Set to reopen in July 2022, the new space will include a vibrant arts café, the Sir Charles Irving Community Art Gallery, and new artists’ studios.

For more staycation inspiration check out our helpful guides: 

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