From headline-making festivals to culinary adventures, landmark anniversaries to unmissable events, 2026 is shaping up to be a standout year in Cheltenham, full of memorable moments.
Across the year, The Festival Town comes alive with a packed calendar of events, activities and new experiences, while its historic streets, leafy parks and independent shops offer plenty to enjoy in between the big moments.
Our elegant Regency Town blends world-class culture, thrilling sporting action and an award-winning food and drink scene with a warm, welcoming atmosphere that invites you to stay a while. Whether you're planning your first trip, returning for a favourite festival or rediscovering the town from a new perspective, discover 26 reasons why Cheltenham is the place to be in 2026...
Images - Montpellier shops and restaurants, The Beefy Boys, East India Café.
Eat, drink and shop
Food lovers are in for a treat in Cheltenham. From award-winning fine dining to buzzing street food, the town offers an unrivalled mix of global cuisine and local flavours. While Cheltenham's mix of independent shops and High Street favourites provides a great shopping experience.
1. Delicious dining
Dedicated foodies searching out the best in fine dining will feel right at home in Cheltenham. The town boasts two Michelin-starred restaurants – Lumiere and Le Champignon Sauvage – who use the finest of ingredients in their exquisite, beautifully presented dishes. While Cheltenham’s rooftop bar and restaurant Nook on Five welcomed celebrity chef John Burton-Race as its new executive chef in 2025.
Looking for something a little more low-key but with equally tasty? Taste the fourth-best burger in the world, The Oklahoma Onion Boy, at The Beefy Boys on Regent Street. Or travel the world without leaving Cheltenham with delicious sushi from KIBOU, Southern Italian dishes at Settebello, and award-winning Indian flavours from The Mahal, Curry Corner and Prithvi.
Cheltenham's food and drink scene always has something new to discover, with Otis & Belle bakery, Rosa’s Thai, Wingstop and Upstairs at the Cheeseworks among those joining the stable in 2025 – and chocolate brand Knoops coming to town in 2026.
2. Award-winning local producers
Cheltenham is also fortunate to be home to many home-grown food and drink producers, several of which have been rated the best in the country.
Among them are Dunkertons, whose Black Fox Cider picked up a gold medal at the 2025 World Cider Awards. You can also drink a toast with Dryhill Vineyard bubbly grown on the slopes of Crickley Hill, a silver award-winner in the Decanter World Wine Awards. Or try a pint of DEYA's Steady Rolling Man pale ale, ranked the Number 1 British Beer of 2024. They all provide tours, where you can learn more about the creative process and try their products on-site.
Local producers can also be found at the Farmers Market on the Promenade twice a month, as well as the Suffolks Sunday Markets several times a year. Whether you’re after charcuterie, cheeses, fresh bakes or local gin, it’s the perfect place to put together a delicious hamper.
3. Cheltenham Food & Drink Festival
A staple of Cheltenham’s busy summer season, Cheltenham Food & Drink Festival in Montpellier Gardens has been bringing people together over a love of good food for the last 18 years. This three-day foodie feast features demonstrations from some of the best chefs and wine experts in the UK, as well as live music, talks, tastings and delicious food.
4. Stand-out shopping
For artisan shops and Regency architecture, head to Montpellier and the Suffolks for boutique gems, from fashion and lifestyle to art and antiques – and plenty of stylish places to eat to go with them. While the Promenade, High Street and Regent Arcade are the places for big brands like John Lewis, Primark, Sweaty Betty, Primark, Hatchards and many more.
It's not all about buying new either. Cheltenham also has a brilliant selection of charity shops where you can bag a bargain while helping out a good cause, which are highlighted in a new map.
Recently securing a third term, Cheltenham BID have been working to promote local businesses and make sure that Cheltenham is a safe, clean, welcoming and vibrant town for 10 years in 2026, and an event to mark the anniversary will be announced in the New Year.
Images - Spring Gallery, Holst Victorian House, GWSR steam train.
Amazing art and history
From its Regency architecture to its contemporary galleries, Cheltenham has a rich tapestry of opportunities to discover and explore the town's history and art.
5. Museums and galleries
Holst Victorian House is a unique insight into the Victorian way of life in the house where composer Gustav Holst was born in 1874. It celebrated 50 years as a museum in 2025 and is offering people the chance to 'Adopt an object' – including the piano Holst composed 'The Planets' on – to help safeguard its future.
Explore the diverse displays at The Wilson Art Gallery and Museum – including a major exhibition exploring the work of Portuguese-British printmaker and storyteller Paula Rego. Throughout 2026, Cheltenham’s Big Museum Project invites visitors to take part in shaping the future of The Wilson before a refresh and reopening in autumn. Or discover Cheltenham's independent art galleries on the Montpellier Art Galleries Trail, which takes you to six galleries showcasing emerging and established artists, with paintings, sculptures, ceramics, glass and more.
You can also learn about Cheltenham’s beautiful architecture and Regency history as a spa town on the free Heritage Trail. This self-guided walking tour takes in some of Cheltenham's most-loved buildings, including the stunning Grade I-listed Pittville Pump Room.
6. Heritage Open Days
Heritage Open Days is the largest, community-led festival of history and culture in England. Every September, Cheltenham gets in on the action, allowing visitors to seek out hidden places and heritage sites across the town that may usually be inaccessible to the public – with this year's theme as 'The everyday history of working lives'. Highlights of the 10-day event normally include Dean Close School, Cheltenham Ladies College, and backstage tours of the Everyman Theatre.
7. Fresh: Art Fair
Britain’s biggest regional art fair, Fresh: Art Fair returns to Cheltenham Racecourse this April, featuring over 50 galleries, 500 artists and over 5000 artworks. It's the only fair outside London where you can browse and buy work by emerging talent alongside famous names like Hockney, Picasso, Matisse and Miro. Expanding in scope every year, there are demonstrations from painters, sculptors and printmakers, interactive workshops and an outdoor Sculpture Park.
8. The Gloucestershire–Warwickshire Steam Railway
Embark on a journey through time to a bygone era of steam power on the GWSR, which travels from Cheltenham Racecourse to Broadway in vintage style. They run a series of special events through the year, from a Rail Ale Festival to the popular Santa Express and the Cotswold Festival of Steam in May – a magical weekend for railway enthusiasts, families and history buffs.
9. Twin town anniversaries
Cheltenham was one of the first towns to forge formal twinning links in the 1950s, and this year it celebrates 75 years of twinning with Göttingen in Germany and 70 years with Annecy in France. These links help foster friendships and connections through social, educational, sporting, youth-related and cultural exchanges. Look out for celebration details to be announced.
Images - Pittville Park boathouse, Cleeve Hill, Leckhampton Hill on the Cotswold Way.
Outstanding outdoor spaces
Cheltenham lies on the edge of the Cotswold AONB (Area of Outstanding Natural Beauty), surrounded by hills and filled with green spaces within. Wherever you are, you’re only a stone's throw away from picturesque walks and natural attractions.
10. Local parks and walks
You don't have to go far in Cheltenham to find a leafy green space to relax in – seven of the town's parks and gardens, including Montpellier Gardens and Pittville Park, gained or retained Green Flag status, an international quality mark recognising the best parks and gardens.
Or lace up your hiking boots and explore the hills around town. Cleeve Hill is the highest point in Gloucestershire, with panoramic views over Cheltenham and the Racecourse as well as a hilltop golf course. Crickley Hill Country Park – jointly owned by the National Trust and Gloucestershire Wildlife Trust – was once the site of an Iron Age Hill Fort and is now a haven for birds, reptiles and mammals. It's a popular place for walkers, easily accessible with an on-site car park and café.
Finally, Leckhampton Hill and Charlton Kings Common features a landscape of limestone grassland that's home to rare orchids in spring. It has a network of walking paths, including a 3km walk suitable for wheelchairs, and is crisscrossed with downhill mountain bike trails for those looking for thrills on two wheels.
Each of the hills also forms part of the 102-mile Cotswold Way walking route between Chipping Campden and Bath if you're looking for a bigger challenge for 2026.
Images - Cheltenham Paint Festival, Cheltenham Jazz Festival, Cheltenham Literature Festival.
Fabulous festivals and events
Rightly known as The Festival Town, Cheltenham hosts a year-round programme of events and festivals. No matter what time of year you visit, there's sure to be something happening.
11. Cheltenham Festivals
Now in its 81st year, Cheltenham Festivals brings together established and emerging artists, writers and thinkers for a public celebration of Jazz, Science, Music and Literature. These brilliant cultural festivals pride themselves on a spirit of curiosity and welcoming bold performances.
2026 has been named the 'National Year of Reading', and this theme will be woven into all four of this year’s festivals. First up is the Cheltenham Jazz Festival at the end of April, which celebrates its 30th anniversary.
The Science festival comes next in June, followed by Music in July, and finally the world’s longest-running Literature Festival in October, which welcomed a record-breaking number of over 100,000 ticket-holders to more than 400 events in 2025.
12. Cheltenham Poetry Festival
Over the last 15 years, Cheltenham Poetry Festival has played host to some of our greatest living poets, spoken word artists, musicians, actors, dancers, writers and film-makers. And it's back in April 2026 for 10 days of readings, workshops and talks which aim to delight and inspire you.
13. Cheltenham Paint Festival
It's hoped that the popular Cheltenham Paint Festival will be back in 2026 – watch this space. In the meantime, you can explore the awe-inspiring street art from previous festivals year-round with the handy Paint Festival app. Featuring a map and audio guide, discover artworks from across the years, from multi-story murals to tucked-away gems you could easily miss.
14. Cheltenham 7s Festival
Bringing people together through music and sport, Cheltenham 7s Festival is a festival like no other. Taking place at Newlands Park this summer, you can join in rugby, netball and dodgeball competitions, or just watch the action from the sidelines while you listen to a line-up of talented artists, bands and DJs, tuck into tasty food and drink, and enjoy family entertainment.
Images - Cheltenham Town Hall, Cheltenham Playhouse, Everyman Theatre
Extraordinary entertainment
Head to Cheltenham in 2026 to discover exemplary entertainment, with top-notch theatre, comedy and dance for everyone to enjoy. The Brewery Quarter also celebrates 20 years as Cheltenham's leisure and entertainment destination in March 2026, with special events to be announced.
15. Live performances
Cheltenham is lucky enough to be home to several incredible theatres and entertainment venues, touting an impressive lineup of performances and shows throughout the year.
Highlights of 2026 at the Everyman include Death on the Nile, The Shawshank Redemption and The Bodyguard. While the Bacon Theatre features back-to-back hits from international tribute acts at K-POP Party, The Dolly Show and Frankie’s Guys.
The Cheltenham Playhouse has a mixture of theatre and music, including A Few Good Men and Fleetwood Mac and Pink Floyd tributes. It's also the venue for Cheltenham's newest festival – the Cheltenham Fringe. This showcase for smaller and up-and-coming theatre-makers returns for its third year in May bigger than ever, with 10 days of music, theatre, film, drag, poetry and comedy.
Finally, Cheltenham Town Hall is the place to see the best in standup comedy in Cheltenham. Big names at the venue in 2026 include Omid Djalili, Sue Perkins and Chris McCausland. It will also host a special concert by Cheltenham Chamber Orchestra in January, who are marking 60 years of championing local talent alongside established artists.
16. Grove Street Community Arts Centre
2026 is an exciting year for the Everyman, as they open a brand-new creative arts education and community centre in West Cheltenham. Grove Street Community Arts Centre will be a vibrant and welcoming community space offering everything from youth theatres and choirs, to dancing and family creative arts clubs, with subsidised arts and culture projects to help local people get creative.
17. Cheltenham Festival of Performing Arts
May sees a big birthday for The Cheltenham Festival of Performing Arts, as the town's oldest festival celebrates its 100th anniversary. The festival gives performers the opportunity to try out their skills in music, dance and drama in the wonderful setting of Cheltenham Town Hall. There's something different every day, from ballet and tap to piano and strings, Shakespeare and poetry.
Images - Wychwood Festival, 2000Trees, Wychwood Festival
Mesmerising music
Cheltenham takes great pride in hosting an eclectic array of music festivals, events and gigs across the year. From alternative to acoustic, heavy metal to classical, all tastes are catered for in our Regency Town.
18. Wychwood
Winner of the 'Best Family Festival' at the UK Festival Awards 2025, Wychwood Festival at Cheltenham Racecourse marks the start of summer in Cheltenham. And there's more to celebrate than ever this year as it marks its 20th anniversary with a headline set from the Kaiser Chiefs. There's plenty more music too alongside comedy, 100+ workshops for all ages, local food and drink, and comfortable camping (hot showers included) beneath the Prestbury Hills.
19. 2000Trees
Another local award-winner is 2000Trees, awarded Best Medium-Sized Festival three years running (2022–2024). One of, if not the best, alternative music festivals in the country, 2000Trees takes place at Upcote Farm in the stunning Cotswold Hills just outside Cheltenham. It's known for its friendly atmosphere, with a sense of common culture, kinship and collective wellbeing bringing this quirky community together.
20. Mini festivals
Alongside the larger-scale events, there are several ‘mini festivals’ each year featuring a diverse range of up-and-coming talent – the perfect way to while away a summer afternoon in Cheltenham.
In June, it’s Exfest at the Exmouth Arms on Bath Road, in July we have the Summer Jam in the Cheltenham Brewery Quarter, the official warm-up for Lakefest Festival, while in September it’s all about FrogFest at the Frog & Fiddle on Cheltenham’s Lower High Street.
Live music can also be enjoyed year-round at Cheltenham venues like the Bacon Theatre, Everyman, Town Hall, Pittville Pump Room, and The Centaur. See what's coming up!
Images - The Cheltenham Festival, Cycling, British Open Snooker
Sublime sport
Whether you’re spectating or taking part, Cheltenham has plenty of sporting events and activities to get your blood pumping in 2026.
21. Cheltenham Racecourse
The home of jump racing, Cheltenham Racecourse features a comprehensive calendar of horse racing action through the year. And it starts from day one in 2026 with the New Year’s Day racing, followed by Festival Trials Day at the end of January.
Then it's time for the big one – the Cheltenham Festival in March. Featuring four days of world-class, heart-thumping action, nothing feels like Cheltenham! The action starts at Champion Day on Tuesday, before Ladies Day returns on the Wednesday with legendary jockey Rachael Blackmore taking the reins as its new ambassador. Then Irish passion raises the rafters on St Patrick’s Thursday before the grand finale at Gold Cup Day on Friday.
The Racecourse also sees a different kind of action in September as The British Open returns to the Centaur for the fourth year running. Promising unrivalled sporting drama and blockbuster clashes, the prestigious world-ranking event is a must-see for snooker fans.
22. Prescott Hill Climb
The Prescott Hill Climb and Bugatti Owners Club, situated between Cheltenham and Winchcombe, is THE place for car lovers. 2026 highlights include the British and Midland Hill Climb Championship, the Motorsport Festival in July and a special event to celebrate the 80th anniversary of the Mini Cooper Car Company in August.
23. Cheltenham Cricket Festival
A highlight of the summer, Cheltenham Cricket Festival is the longest-running cricket festival in the world, with its first match being played between Surrey and Gloucestershire in 1872. Set amongst the manicured grounds of Cheltenham College, this quintessentially English event is a great attraction for avid cricket fans, new supporters and big cricketing stars.
24. Cheltenham Town FC & Gloucester Rugby
With a packed schedule of matches across the two venues – and 7000- and 16,000-capacity stadiums respectively – football and rugby fans are spoilt for choice in Cheltenham and Gloucester. Catch Cheltenham Town in action against Leicester City in the FA Cup Third Round on 10 January. Or rugby fans won't want to miss the Premiership Rugby Cup match against local rivals Bristol Bears on 1 February.
25. Running, cycling and more
Prefer to join in? If you want to improve your fitness in 2026, there are plenty of opportunities to take part in sport in Cheltenham. Runners can test themselves at Cheltenham Running Festival and Run Cheltenham, whether you're running your first 5k or taking on a Half Marathon. Or why not raise money for charity by joining in the 22-mile Cheltenham Three Peaks hiking challenge or the Ride For Ryder Sportive cycle ride?
Images - Gloucester Docks, Cotswold Farm Park, Lower Slaughter in the Cotswolds
Beyond Cheltenham
As well as the huge array of things to do within Cheltenham, the town is also an ideal base to get out and explore the surrounding area, with the Cotswolds, Forest of Dean and Wye Valley, Malvern Hills and more all within easy reach.
26. Cheltenham day trips
The Romantic Road: Named by The Telegraph as one of the Great British Drives, the Cotswold Romantic Road is a driving route which takes starts in Cheltenham and takes in some of the highlights of the Cotswolds across one or two days, with cosy pubs, rolling hills, historic landmarks and charming Cotswold towns and villages along the way.
Tewkesbury (20 minutes away): Tewkesbury is most famous for its Norman Abbey, with 15th-century stained glass and unique roof bosses. Learn about the beautiful riverside town’s local history at the Heritage Centre or join an army of enthusiasts at Tewkesbury Medieval Festival.
Gloucester (25 minutes away): Visit spectacular 11th-century Gloucester Cathedral, whose magnificent new organ will be unveiled at a special festival this June. Or travel back through time at Gloucester’s Historic Docks, whose original late-Victorian warehouses have found a new lease of life. There’s dining at Gloucester Food Dock and local history at the National Waterways and Soldiers of Gloucestershire museums.
Stroud (30 minutes away): A haven for creatives, Stroud has plenty going on when it comes to the arts. The annual Stroud Arts Festival brings top-class music, poetry, drama, art and dance to the town in June and October. The month-long SITE Art Festival gives a glimpse into artists’ homes and studios. And the town is also home to an award-winning Saturday Farmers' Market.
Cotswold Farm Park (30 minutes away): Cotswold Farm Park makes a brilliant family day out, with lambs to feed and rabbits to cuddle. Adam Henson’s farm is the home of rare breed conservation, where you can meet animals from Gloucestershire Old Spot Pigs to Highland Cattle. There’s also a variety of indoor and outdoor play areas, wildlife walks and an on-site restaurant.
With so many reasons to head to Cheltenham in 2026, why not book a stay? Check out our guides to help plan your trip:
