Character Cottages

Things To Do and See In Cheltenham


Welcome to the cultural capital of the Cotswolds, Cheltenham. Enjoy a jaunte around the upmarket Montpellier Quarter or arrive at Cheltenham Races via steam train. Book a holiday in Cheltenham or the surrounding areas and you may actually return home with an even longer ‘must-see’ list. From special occasion boutiques and upmarket eateries and famous festivals, it goes without saying, there’s lots to make you smile in Cheltenham. Here we take a look at our favourite.

Theatre for all Seasons

New for 2019, join Sir Ian McKellen in Cheltenham’s top entertainment venue, the Everyman Theatre, as the actor celebrates his 80th birthday in his “most difficult work yet”.

Rather than hiding behind the comfort of feature length films, such as Lord of The Rings, McKellen is choosing his birthday celebrations to deliver what he calls the biggest test of his career - a touring one-man show. And not only that, he is using the occasion to raise money for best-loved theatres around the country. One of which is the Everyman Theatre in Cheltenham. Profits from his Cheltenham show, running on the 7th and 8th May 2019, will be donated to the theatre’s Education and Outreach Department.

A true ‘theatre for all seasons’, the 120-year-old Everyman Theatre has one of the best theatre production line-up’s in the UK. There’s quite a delectable choice too, from a night of ballet, comedy, dance, opera or drama. And of course seasonal performances like family pantos are a must on your Cotswold holiday itinerary.


Haute Cuisine

If you’re on holiday in a large group and perhaps celebrating a special occasion, why not make a private reservation at one of Cheltenham’s newest artisan eateries, such as Woodkraft, which newly opened November 2018.

Located in the cultural heart of Cheltenham on Regent Street, just doors away from the Everyman Theatre, Woodkraft is the second restaurant by Simon Wood, MasterChef Champion 2015.

You may also want to reserve a table in The Ivy Montpellier Brasserie, which has recently found its home in one of Cheltenham’s most iconic buildings. The stunning Montpellier Rotunda was built in 1817 to house Montpellier Spa and was designed to impress and rival the nearby Royal Well spa. Today, a dazzling circular bar sits at the centre of this restaurant, with light from the huge dome above creating a truly unique theatrical dining space, that was in fact, inspired by Rome’s Pantheon.

The Ivy Montpellier

Cheltenham Races & Steam Train

In hot pursuit of Aintree and Ascot, Cheltenham Racecourse is one of the largest horse racing stadiums in the UK. Set in a ‘natural amphitheatre’ below Cleeve Hill (the highest in the Cotswolds) and with its own steam train station, Cheltenham Races is quite the scenic racing attraction.

Coinciding with St Patrick's Day in March, the prestigious 4-day Cheltenham Festival meeting is a highlight in the racing calendar, with race prize money second only to the Grand National. The famous “Cheltenham roar” is an experience in itself and there’s a busy non-racing events calendar to consider also, including the Wychwood Festival.

Cheltenham Races is an ideal holiday day trip as a day at the races is so much more fun as a group. Plus, there’s the added bonus of arriving by steam train. Buses run regularly from Cheltenham town centre to Cheltenham Racecourse Train Station. The racecourse station sits on the southern point on the 28 mile scenic route through the beautiful Cotswold countryside, taking in Winchcombe, Toddington and Broadway. 

Cheltenham Spa Steam train

Pittville Park

Lying two miles outside of Cheltenham town centre towards Cheltenham Racecourse, is Pittville Park - a sprawling 100 acre recreational estate showcasing the town’s glorious healthy-giving waters. The Victorian suburb of Pittville was opened in 1825 and was designed to rival all of Cheltenham’s spas, with its own Pump Room spa, aviary, lake boating and manicured gardens and estate. Today it is the largest ornamental park in Cheltenham, and is a great place for families to picnic and for little legs to let off some steam. It is a dog friendly park and the newly renovated children’s outdoor play area is clean and well kept. There are two scenic lakes with lots of wildlife. There’s one hour row boat hire, tennis courts and pitch-and-putt golf too. Pick up a picnic blanket for free from the award-winning cafe, Central Cross Cafe.

Cheltenham Lido

Mineral springs were discovered in Cheltenham in 1719 and ever since the spa town has attracted visitors looking for a healthy holiday. And in 1930’s Britain, lidos were in their heyday. Joining the trend for open-air swimming and holidaying in the UK, Cheltenham lido was originally built in 1935. Restored in 1996, this is one of Cheltenham’s true gems.

It is a beautifully maintained Art Deco lido set in four acres of wonderful English landscaped grounds. Plus it is heated! The 50m pool is kept at 26 degrees and the children's pool is heated to 30 degrees, making it a perfect holiday day trip. In fact, Sandford Park Lido was nominated in 2018 for Best Active Day Out With The Kids by Day Out With The

Fans of the benefits of cold water open-air swimming can enjoy the 50m pool during October, where the water temperature drops to 21 degrees.

With poolside table tennis, lawns for soaking up the sun from your swimming towel, kids pool with slide, and a cafe serving hot and cold food, the lido in Sandford Park is also quite the place ‘to be seen’.


Montpellier District

Cheltenham is ‘Britain’s most complete Regency Town’, and the Montpellier District is the best place to head to to take in some seriously impressive Regency architecture. Today, this is a laid-back and fashionable shopping quarter, where visitors relax and unwind in Michelin star restaurants, bistro bars and eclectic boutique shops.

The Neptune Fountain, modelled on the Trevi fountain in Rome, is one of Cheltenham’s most iconic landmarks and sits at one end of town’s famous Promenade and parallel Long Gardens. Named as one of the top five shopping streets in the UK, here you’ll find the likes of Jo Malone, TOAST, L.K. Bennett and Hotel Chocolat.

As well as shopping, we’d recommend taking in the beautiful avenue of trees, sitting by the memorial of the famous Antarctic explorer Edward Wilson in the shade of the canopy of elm and horse chestnut trees. Look out for the street art, The Minotaur and the Hare also.

Along with being the ‘place to be seen’, The Parade and following on into the Montpellier District is where you will find the beautiful Imperial Gardens, which are flanked by Regency architecture.

This pleasure garden was built for the fashionable guests of Cheltenham’s first spa, the Sherborne Spa (now the Queen’s Hotel), which look onto the gardens. Little has changed, with live music and literary events taking place from The Garden Bar and visitors relaxing in the formally planted gardens around the original central fountain.

Soak up the French atmosphere on the bar and boutique-lined Montpellier Street.

Along Montpellier Street you’ll find more impressive Rome-inspired architecture, and will want to look up the Montpellier Rotunda, a Grade I listed building with a dome inspired by Rome’s Pantheon (now home to The Ivy Brasserie). The region’s oldest shopping gallery, Montpellier Arcade, is found here too.

You can then enjoy a distinctly French atmosphere, taking in upmarket shops and restaurants, including Le Champignon Sauvage – a contemporary French, 1 Michelin Star, 4 AA Rosettes, Sunday Times Top 100 listing. Lumiere offers modern British cuisine and holds 3 AA Rosettes. Translated as ‘search’, Rechercher is a French interior décor and home furnishing shop that we like to look up. 

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