Things to Do in Cheltenham

Things to Do in Cheltenham

Cheltenham in Gloucestershire is a very pretty, affluent Cotswold town, well worth a visit for its beautiful parks, fabulous shopping, excellent restaurants and host of festivals. Seeped in Regency architecture, it’s a gorgeous town that is often compared to Bath, but being on a smaller scale offers a more intimate feel.

Easy to explore on foot, Cheltenham is a vibrant town, famous for its festivals, restaurants, colleges, architecture, theatres and racecourse. Lying on the fringes of the Cotswolds National Landscape, its within easy reach of many major cities and towns yet offers a tranquil bubble in which to enjoy countryside and culture in equal doses. From its stunning Regency shopping promenades to its flower-peppered parks, it has something for everyone. Needless to say, if you’re looking for somewhere to enjoy a short break or luxurious holiday, you need look no further. 


While Cheltenham is a thriving hub today, its story doesn’t start here. Beginning life as an Anglo-Saxon village more than 1,200 years ago, it thrived as a market town for many centuries, before the discovery of mineral springs in the 18th Century transformed it into a health and holiday spa town. With its waters widely recognised for their health-boosting properties, Cheltenham rapidly became one of the most famous spa towns in the UK and its population exploded from 1500 people in 1700 to 35,000 by 1850. Among the people flocking to drink from its healing waters were many famous names, including the then Princess Victoria, Jane Austen and Lord Byron. While drinking from its springs are no prerequisite today, the town, along with many of its surviving Regency terraces, crescents and promenades, still affords a wonderful place to relax and revive.

Things to Do 

If you are planning a holiday in or trip to Cheltenham, you’ll find yourself spoilt for choice for activities and attractions. Here are the best things to see and do in Cheltenham. 

The Brewery Quarter

If you’re looking to entertain the children and hit your favourite high street eateries and shops, look no further than the Brewery Quarter. Conveniently located in the centre of town, this one-stop shop of wonders is home to all kinds of popular restaurants, bars and family-friendly attractions, including an Imax cinema, bowling alley, indoor adventure golf and children’s soft play area. 

Cheltenham Racecourse

Cheltenham Racecourse lies on the outskirts of the town, overlooked by the gorgeous Cleeve Hill. As well as seasonal racing, the venue puts on a range of events throughout the year, including well-known artists, musicians, comedians and more. If you’re visiting mid-March, expect the town to be heaving with activity ahead of the annual Gold Cup, a famous four-day racing event. 

Cheltenham Theatres 

Cheltenham has a long-established arts and music scene, at the centre of which are its theatres. For a year-round calendar of events, keep an eye on the upcoming productions and performances at the Everyman Theatre, the Playhouse and the Bacon Theatre. From the dramatic to the hilarious to the slightly surreal, performances are guaranteed to enthral all generations. 

Cheltenham Town Hall and Imperial Gardens

Cheltenham’s town hall is a versatile entertainment space that should be on everyone’s list of places to visit in Cheltenham. Book tickets to see one of the many events staged inside the town hall itself, or head outside to explore its adjoining Imperial Gardens. Here, a brilliant Garden Bar, Orangery and walled garden await for exploration, recreation and mastication. 

Gloucestershire Warwickshire Steam Railway

The Gloucestershire Warwickshire Railway provides a brilliantly nostalgic experience for visitors of all ages. Operating steam and heritage diesel trains from its Cheltenham station, it offers a uniquely romantic way to soak up the picturesque, honey-stone villages and rolling countryside of the Cotswolds and admire views of the billowy Malvern Hills. 

Holst Victorian House

Cheltenham is the birthplace of composer Gustav ‘The Planets’ Holst and there’s a lovely little museum in the house where he lived close to Pitville Gates. The town’s only preserved Victorian home open to the public, Holst Victorian House showcases the building’s rooms as they would have been during Gustav’s childhood and features period furniture and family artwork. 

Montpellier District

The Montpellier District is one of Cheltenham’s most attractive shopping districts, characterised by gorgeous Regency architecture and immaculately manicured gardens. As well as its array of historic buildings, its most well-known features include its Caryatids: 'armless ladies' stone sculptures inspired by the Acropolis in Athens. Pull up a seat at one of the district’s bars or cafés for a spot of alfresco refreshment. 

Montpellier Gardens

The 19th Century Montpellier Gardens are a real beauty spot. Comprised of two zones, it features a southern zone with lots of recreational facilities (think: bandstand, tennis courts, children’s play areas, art gallery…) and a northern section with green spaces and an arboretum (think: picnics under balmy sunshine and strolls through the trees).

Pittville Park and Pump Room

Head along Winchcombe Street to arrive at the Pittville Gates, flanked by regal Georgian houses. Here a winding ribbon of path leads you through a verdant park peppered with rare trees, before leading you to a boating lake and onwards uphill to the pretty Pittville Pump Rooms. If it’s a sunny day, a picnic is lovely on the lawn, otherwise you can check out the Central Cross Cafe for tea and cake.  

The Promenade and Long Gardens

Voted as one of the UK’s top five shopping streets, Cheltenham’s Promenade with its tree-lined avenue, smart shopfronts and seasonally evolving Long Gardens is a must-see. Dating back to 1818, the street has retained much of its original beauty and style, with modern bars, trendy cafés and independent boutiques blending sympathetically into its attractive historic façade.  

Sandford Park and Lido

If you are looking to capitalise on Cheltenham’s green spaces and outdoor activities, then you should definitely pop Sandford Park on your list of things to do. With its grassy swathes, water fountains and flower beds, the park itself provides a little bubble of tranquillity. Meanwhile, the real star of the show is the 50-meter, 1930’s outdoor swimming pool, complete with its original turnstile!

The Wilson - Cheltenham Art Gallery & Museum

Cheltenham Art Gallery & Museum, also known as the Wilson, is a superb attraction in Cheltenham. As part of its exhibitions, it displays Arts and Crafts, decorative art and fine art collections, as well as information about Cheltenham’s rich history. Perhaps most popular are its features on Cheltenham-born explorer and artist Edward A. Wilson, and Emery Walker Library.

Cheltenham’s Festivals 

Cheltenham boasts some fantastic festivals that span a wonderfully eclectic array of themes. Each year, there is the Cheltenham Jazz Festival in April/May, Science Festival in June, Music Festival in July and Literature Festival in October. During the summer, Montpellier Street hosts a day fayre, while in winter, the scene is transformed into a magical wonderland in the form of Christmas markets.

The Cotswolds 

Situated on the edge of the Cotswolds National Landscape (formerly AONB), Cheltenham is in an ideal location to explore the area. If you’d like to head into the heart of the Cotswolds, hop aboard the Gloucestershire Warwickshire steam railway or take a spin in the car and discover its picture-perfect villages, market towns and patchwork countryside lined with hedgerows and peppered with tufted trees. If you do choose to travel by car, you can also consider picking up the circular driving loop known as the Romantic Road. Spanning 45 miles in total, the loop gives you the chance to cruise past Cotswolds highlights and stop off at favourites along the way. 

Places to Eat

With Cheltenham being one of the country’s foodie hotspots, you have rich pickings when it comes to eating out. Michelin star Cotswolds eateries like Le Champignon Sauvage and Lumiere are at the top of the list. The Daffodil, a glorious art deco eatery in a former cinema, is a great choice for dinner with a twist, while Prithvi and Curry Corner both offer fantastic Indian dishes. For the full low-down on the best places to eat in Cheltenham, read here

Feeling inspired? Take a look at our luxury cottages in Cheltenham here.


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