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

5 musts for your 2020 visit to Cheltenham

Mothers Day – Sunday 10th March 2024 

Visit a festival

Cheltenham is widely regarded as the ‘Festival Town’ and so you would be surely unlucky to visit with an empty diary. Ranging from the renowned Literature and Horse Racing to the Science and Food festivals there is a festival for everybody. Here’s some of our favourites.

Literature Festival – For ten days every Autumn (2-11 October 2020) Cheltenham is transformed as the town welcomes over 600 of the world’s finest writers, actors, politicians, poets and leading opinion formers to celebrate the joy of the written word. Where else could you see the Gruffalo, an award-winning novelist, or a Hollywood legend exchange views with political leaders? Established in 1949, The Times Cheltenham Literature Festival is one of oldest literary events in the world – and with a feast of superstar speakers, an unrivalled setting at the heart of Cheltenham, and the chance to meet your favourite authors and characters – it’s certainly the most fun! The festival takes place at several locations around the town. Most venues are within a short walk of The Portland Guesthouse. Limited details have been released for 2020 however full details as and when they are released can be found here:

The Cheltenham Festival

The most prestigious and unmissable Jump racing event of the year, creating an unrivalled atmosphere in the town as over 265,000 visitors are attracted to Cheltenham. Four days of racing will be concluded on Friday 13th March 2020 with Gold Cup day. Cheltenham racecourse is located under a mile from The Portland Guesthouse and as traffic can build up quickly, a walk is usually quicker and more encompassing of the atmosphere.

Full details and last remaining tickets for any of the 2020 race meetings can be found here:

Cheltenham wellbeing festival

Returning in September 2020 for its second year, the festival is a week-long celebration of wellbeing. Talks, workshops, treatments and more can be expected from several venues around the town. With full 2020 details yet to be released keep an eye our here: or sign up for their newsletter.

Jazz Festival

Festival-goers can see some of the music scene’s biggest names and best emerging talent in the Big Top and Jazz Arena. With free outdoor music and fun family activities, Montpellier Gardens is the place to soak up an outstanding festival atmosphere. Less than a mile from The Portland Guesthouse our guests can enjoy the walk through Cheltenham in the usually fair May weather. This year’s festival will take place on the May day bank holiday weekend from 5th-10th May 2020.

Full details as they are released can be found here:

Music Festival

If Jazz is not your genre then come 3rd-12th July Cheltenham’s music festival is a treat for the ears with high-calibre performances, magnificent venues and a huge variety of music on offer. On the opening weekend of the festival, three days of free concerts, pop-up performances and showcases in Imperial Square can be enjoyed by all.

Enjoy a performance

Cheltenham boasts three theatres; Everyman, Cheltenham Playhouse and Bacon. Each offering spectacular shows and performances.

The Everyman Theatre, located on Cheltenham’s Regent Street in close proximity to the High Street is a Victorian venue with an ornate 658-seat auditorium, a 66-capacity studio plus a cafe and 2 bars. 2020 at the Everyman includes Thriller Live!, The Elton Show, Comedy from Chris Ramsey, David Baddiel and Chloe Bezer. Families will enjoy Shrek, Jack and the Beanstalk and the wonderful wizard of Oz amongst others. Get your feet tapping and hands clapping with Six the musical, On your feet and Priscilla – Queen of the desert amongst the musicals for 2020. To find the perfect show for you visit: The Everyman theatre is roughly 10 minutes’ walk from The Portland.

Cheltenham Playhouse is the town’s intimate community theatre, located on Bath road, a short 15-minute walk from The Portland. The Playhouse is owned by Cheltenham Borough Council but has been run by volunteers since 1958. 2020 plays include Goodnight Mr Tom, Jekyll & Hyde and Bombshells. Also, in the diary are musicals, dance & music shows including The Counterfeit Sixties, films, workshops and talks.

For the full list of dates visit:

The Bacon Theatre is on the site of Dean Close School, a co-educational day and boarding school. Shows featured for this year include; The Tina Turner and Aretha Franklin story, The adventures of Rapunzel and The Beach Boys tribute.

See their full calendar here:

Parks and Outdoor spaces

The town is privileged to have several parks and gardens. Whilst Montpellier and Imperial gardens home many of the town’s festivals, when they are unoccupied both provide refreshments and a relaxing environment.

Montpellier gardens are surrounding by many grade1 listed buildings, a feast for the eyes taking in the regency atmosphere. Imperial gardens were established for the ‘wealthy’ residents to have a pleasure garden. Again, the regency feel continues around the garden.

Across town you can take to the water at Pittville park’s boating lake. The lake also plays host to fishing during the season. Other activities in the park include; tennis courts, children’s play park, and aviaries. The pump room also resides in the park listed as a grade 1 building it oversees the Eastern side of the park. If you are heading out to explore the town’s open spaces be sure to talk to the Portland team who will be able to make some weather dependant recommendations.


We have a balanced combination of independent and well-known high-street brands filling the town, your day (or even more!) will be filled with browsing.

Big names including John Lewis, House of Frazer and Marks & Spencer’s mingle with smaller names including Mann Jewellers, Keith Scarrott Shoes and East Lifestyle in the High Street & Promenade.

Other shopping areas in the town include Bath road and Tivoli, Montpellier and the regent’s arcade with the famous Wishing Fish Clock.

Holst Birthplace Museum

Take a two-minute walk from The Portland and you’ll be transported to the 19th Century, and the birthplace of composer Gustav Holst. The museum houses the piano he composed ‘The Planets’ on and Victorian kitchen, bedroom, scullery and nursery.

A range of exhibitions run throughout the year; the museum reopens Tuesday 18th February 2020.