The Portland Guesthouse, 51 Portland Street, Cheltenham, GL52 2NX. Telephone: 01242 906 600

Things To Do In Cheltenham

Mothers Day – Sunday 10th March 2024 

Cheltenham Racing – The Home of Jump Racing

“Cheltenham is at the heart of almost every aspect of Jump racing. This is the place where owners, trainers, jockeys, stable staff and breeders dream of having winners. It’s the place where the most important races are run. This is where many stars of the future go through the sale ring. But most of all, this is the place where the equine and human champions forge their reputations.

As always, there is much to look forward to in the season, with 16 exciting days of top-class Jump racing. Hundreds of thousands of racing fans come to Cheltenham every year, but you don’t need to be an expert to make lasting memories.

The wide variety of experiences range from the relaxed feel of the meetings in October and April to the heady excitement of The November Meeting and the family fun of New Year’s Day.

However, the focus of any Jump season is always The Festival™ presented by Magners. The Festival at Cheltenham is the shining jewel in Jump racing’s crown. It is four days of magic, magnificence, and madness, played out on a stage framed by the breath-taking vista of the Cotswold Hills. It features a cast of the best horses, jockeys, and trainers playing to an audience of 260,000 people, all of whom are determined to have the time of their lives.” –

Key Dates for racing in 2020

  • New Year’s Day – Wednesday 1st January
  • Festival Trials Day – Saturday 25th January
  • The Festival (Preview Evening, no racing) – Sunday 8th March
  • The Festival – Tuesday 10th – Friday 13th March
  • The April Meeting – Wednesday 15th & Thursday 16th April
  • Race Night featuring Hunter Chase Racing – Friday 1st May

Alternative entertainment at Cheltenham Racecourse in 2020

  • Coral Snooker World Grand Prix – 3rd February
  • Cheltenham Masters Darts Tournament – 21st February
  • A tribute to Tina Turner – 28 February
  • Cheltenham Running festival – 7 June
  • Cheltenham Challenge 14th June
  • Jason Donovan – 15 September

Cheltenham Town Hall

“Rich in heritage, opulence and vibrancy, our much-loved jewel of Cheltenham sets a stunning backdrop for an impressive year-round events programme.” –

Key dates for 2020

  • A Country Night in Nashville – Friday 10th January
  • Bye Bye Baby – Friday 17th January
  • Elkie Brooks – Saturday 18th January
  • From the Jam – Friday 24th January
  • The Classic Rock Show – Tuesday 28th January
  • Fisherman’s Friends – Saturday 8th February
  • The Banff Mountain Film Festival – Wednesday 12th February
  • An Evening of Marvin Gaye – Saturday 15th February
  • Rumours of Fleetwood Mac – Monday 9th March
  • Boyzlife – Thursday 26th March
  • Rob Brydon – Tuesday 21st April
  • National Symphony Orchestra – Sunday 24th May
  • Tony Adams – Thursday 28th May

Cheltenham Festivals

“Cheltenham Festivals is a charity which feeds the human spirit. Its participation programmes reach out year-round and culminate at the town’s internationally-acclaimed Jazz, Science, Music and Literature Festivals.” –

  • Jazz Festival – 5th – 10th May
  • Science Festival – 2nd – 7th June
  • Music Festival – 3rd – 12th July
  • Literature Festival – 2nd – 11th October

Royal International Air Tattoo

“The World’s Greatest Airshow! Few events can rival the intensity, drama, and spectacle on offer at the world’s greatest airshow. The Air Tattoo returns next July to RAF Fairford.” – 17th – 19th July

Everyman Theatre

“The Everyman is Gloucestershire’s theatre – and has been serving the county (and beyond) since 1891.

Our main auditorium is an architectural masterpiece designed by Frank Matcham that has inspired generations of performers. The common thread throughout the many years has always been our relationship with our audience – a relationship that we treasure.

Whether you visit the Everyman to see ballet, opera, drama, dance, comedy, music events or our traditional family pantomime. Or if you take part in one of our many community projects, education workshops or youth theatre productions. Or if you visit us to dine or drink in our café, or wine bar. Or if you are simply here to visit our website and book your tickets. Whatever the reason we would like to warmly welcome you and hope you return many times.”

  • Cinderella – Until Sunday 12 January
  • Gladys Knight: Midnight train to Georgia – Friday 17th January
  • The Croft – Wednesday 22nd – 25th January
  • Rain or Shine: The Wind in the Willows – Friday 24th – Saturday 25th January
  • Six the Musical – Monday 27th January – Saturday 1st February
  • Shirley Valentine – Thursday 13th – Saturday 22nd February
  • The Elton Show – Friday 17th April
  • Chris Ramsey – Sunday 17th May
  • Priscilla:  Queen of the Desert – Monday 18th – Saturday 23rd May

Holst Birthplace Museum

“Explore Cheltenham’s historic house, the Holst Birthplace Museum, where composer Gustav Holst was born in 1874.

The house is a time capsule of 19th century life with a working Victorian kitchen, Victorian bedroom, scullery and nursery.  Visitors can also experience a Regency Sitting Room, of the type popular when Cheltenham was a fashionable spa town. It is the only Regency domestic room open to the public in the town and contains an impressive art collection.

Composer Gustav Holst’s life and times can be discovered in his Music Room, complete with the piano he composed The Planets on.

The museum hosts a range of exhibitions, events and children’s activities throughout the year, including its popular ‘Bake Back in Time’ events using the working coal-fired range.” –

The Wilson – Cheltenham Art Gallery & Museum

“The Wilson – Gloucestershire’s premier art gallery and museum. Home to an internationally significant museum collection of exceptional quality and variety, changing displays of our Designated Arts and Crafts Movement collection, fine art collections, and The Open Archive, which houses our fascinating archives relating to Antarctic explorer Edward A. Wilson, Cheltenham’s history, and the Emery Walker Library.

We’re home to the Wilson Arts Collective, de Ferrieres community gallery, and brand new inclusive World of Wonders! gallery.”

Pittville Park

“Opened in 1825, Pittville Park is the largest ornamental park in Cheltenham and features the magnificent Pump Room and lakes. This park is given a grade 2 listing under the English Heritage register of historic parks and gardens, with the Pump Room as a grade 1 historic building.

Pittville Park is divided in two by Evesham Road. Most people are familiar with the eastern side of the park, which is overlooked by Pittville Pump Room, and home to the main children’s play area and the aviaries where you’ll find our popular birds and bunnies. However, to the west of Evesham Road lies the much larger western park with its more natural layout and small areas of woodland. Here you will find the larger ‘lower lake’ where you can fish during the fishing season, and there is a smaller children’”.