17 Quirky Things to do in Cheltenham for a Colourful Autumn Weekend

Posted on 12th Oct 2020. In , , ,

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“I have rarely seen a place that so attracted my fancy,” Charles Dickens once wrote of Cheltenham on one of his provincial reading tour visits to the town.

Much of today’s Cheltenham would still be familiar to Dickens. The incredible Regency architecture continues to dominate the town (it is, according to Visit Cheltenham, ‘the most complete Regency town in Britain’), as does the sophisticated air left behind by the Georgians who came to take in the ‘spa waters’ in the 18th-century.

These days, of course, you can add many more unique, quirky and modern attractions to your list of things to do in Cheltenham. Alongside the beautiful buildings, there are world-class festivals, incredible local restaurants, bars and cafes, independent shops and a buzzing cultural scene.

Best of all, Cheltenham is very much alive all year-round. Come autumn, the town’s heartbeat doesn’t slow to a resting pace: free heritage tours, vibrant festivals and seasonal events take over from where the summer season left off.

So, if you’re looking for things to do in Cheltenham on an autumn weekend break, you won’t be left short of choice – and to help you plan your trip, here are some of our favourite options.


Things to do in Cheltenham

Hang out with Banksy’s contemporaries

On the 1st weekend of every September, over 100 of the world’s most celebrated street artists hit the pavements of Cheltenham to take part in the annual Cheltenham Paint Festival. Armed with cans of paint and bags of talent, these local, national and international artists transform venues throughout the town creating a large-scale free outdoor gallery of incredible artwork on buildings, bridges, tunnels and walls. There are even spray-painting workshops for kids to get involved.

Many pieces created as part of the Cheltenham Paint Festival are permanent, so even if you miss the live action you can still take a 6k street art trail around the town and see the work long after the artists have left.

Do: Walk or cycle the trail using the map to tick off the sights – and remember to get a selfie by the ‘I Love Cheltenham’ mural on the town’s Honeybourne Line (the old railway route connecting Cheltenham and Honeybourne, Worcestershire).


Things to do in Cheltenham

Sip the Spa Waters Like an 18th-Century King

Like Bath, Cheltenham is best-known as a spa town, primarily because of King George III, better known as Mad King George. He came to Cheltenham in 1788 and spent five weeks in the town, taking the waters for his health. His visit sealed the town’s popularity amongst wealthy Georgians who flocked to do the same, holidaying in Cheltenham’s handsome townhouses, ‘promenading’ the tree-lined avenues and drinking the medicinal waters at the nearby spas.

Visitors would sup the waters – England’s only source of naturally alkaline water – either at the original spa site or at one of the rival spas that sprung up in fashionable Montpellier or Pittville. Sadly, the site of the first spring is now underneath the Cheltenham Ladies’ College and not accessible, but you can still sample Cheltenham’s famous water today if you head to Pittville Pump Room.

Do: Take advantage of the free Heritage Open Days events that run around Cheltenham every year in Sept. Heritage Open Days is England’s largest festival of history and culture, where places across the country throw their doors open to celebrate their heritage, community, stories and experiences.

Book a place on one of the guided tours or talks taking place in Cheltenham to learn more about its Regency heritage, the incredible buildings (including the Pittville Pump Room) and the many famous visitors.



Things to do in Cheltenham

Pitch up for an Autumn Picnic in the Former Winter Gardens

Cheltenham is blessed with an abundance of award-winning parks, gardens and tree-lined avenues to explore, which are especially glorious as autumn arrives in the town. Spring greens give way to succulent reds and the low sun paints the stones terraces and statues in a soft light.

Many of the parks in Cheltenham herald from the Regency era when they were planted as ‘pleasure gardens’ for the wealthy. The town even had its own ‘winter gardens’ in the 19th-century on the site of today’s Imperial Gardens (just off the Promenade, at the rear of Cheltenham Town Hall), but it was demolished in the Second World War to frustrate Luftwaffe navigation efforts.

Our favourites Cheltenham parks are Montpellier Gardens (with its bandstand, community art gallery and café), Imperial Gardens and Pittville Park, home to the Pittville Pump Room, lakes and a large bird aviary.

Do: Take a picnic to Imperial Gardens on a crisp autumn day. This beautiful park is encircled by elegant Georgian townhouses and studded with formal flower beds, which were laid out in a formal style just after WW2.

There’s also a bar, The Garden Bar, where you can enjoy a hot drink whilst watching the world go by. Be sure to check out the Gustav Holst memorial fountain, too; the composer was born in Cheltenham in 1874 and is famous for his composition The Planets.


Things to do in Cheltenham

Meet some of the world’s greatest writers and thinkers

For book lovers, The Times and The Sunday Times Cheltenham Literature Festival is an absolute must on your list of things to do in Cheltenham.

This world-famous literature festival returns to the town every October, bringing with it the world’s greatest writers and thinkers. The festival unfolds over 10 days in tented villages set-up in Montpellier Garden and Imperial Gardens; although during Covid the festival became a hybrid of live events and digital broadcasts – which you can still experience until 31st December online with a one-off £20 subscription for over 120 events!

Over the years, the festival has welcomed authors, poets, biographers, journalists and celebrities, including Hilary Clinton, Sir David Attenborough, Leonard Cohen, and Salman Rushdie, and given locals and visitors to Cheltenham the chance to interact with award- winning authors and see up-and-coming writing talents.

As well as the talks, there are other scheduled events and workshops so that children and adults can flex their creative muscles. And, of course, there are plenty of pop-up food and drinks options to ensure a fabulous day out.


Things to do in Cheltenham

Take Tea like the Ancient Chinese did

When it’s chilly outside, warm up with tea – with a difference. Head to August Moon Teahouse in Montpellier Court and experience a traditional Chinese tea ceremony, led by owner, Estelle Liu.

The ancient Chinese held tea in high regard for its medicinal properties. They prized teas grown high on the mountains, in crags and crevices in the rocks – and they believed tea was best brewed with pure, clean, mountain spring water, and that fire should be from clean and natural sources.

As such, the process of making a traditional pot of tea in China is about achieving the right mix of environment, people to share the tea with, water, fire, skills, and utensils. Fortunately, with Estelle as your guide, you don’t need to be an expert.

She’ll share the history, philosophy and principles of Chinese tea with you, carefully guiding you through the tea-making process using the finest tea and handmade porcelain brought to Cheltenham from China. It’s a mindful, soulful experience that’ll mean you’ll never look at tea in the same way again.


Things to do in Cheltenham

Forage for Your Supper then Feast like a King

Autumn is the perfect time to get up close and personal with the bounty that grows all around us, so book yourself onto a foraging experience around Cheltenham’s green spaces or the surrounding countryside. Local foraging expert, Rob Gould – The Cotswold Forager – runs a variety of public and private walks in and around Cheltenham throughout the year.

He’s a warm, gentle, knowledgeable guide who is passionate about nurturing a love for the outdoors, reconnecting people with their natural environment and helping them understand the benefits of wild food.

With over 20 years’ foraging experience, Rob shows you the edible plants and flowers that grow wild in urban spaces, such as central Cheltenham, as well as sharing recipes so you know how to cook and preserve your wild harvest.

DO: Look out for Rob’s fabulous forage and feast events. This experience combines a 1.5hr – 2hr urban foraging walk with a multi-course meal cooked by a local chef and based on the wild delights you’ve harvested. Ideal for hungry brains and bellies.


Things to do in Cheltenham

See the Secret Barbara Hepworth Sculpture

Barbara Hepworth was one of the 20th-century’s greatest sculptors. In the 1960s, when she was at the height of her fame and fortune, she was approached by the Cheltenham & Gloucester Building Society to create a sculpture for the its new headquarters in the town.

Despite her international status, she didn’t decline the offer and took up the challenge creating a sculpture for the curved offices that remains there to this day (above Wagamamas).

The 50-year old sculpture, called Themes and Variations, is made from three bronze semi-circular forms and is unusual for the artist because it is 2D (Hepworth is best known for works which people can walk around and see through). However, walk past it on the opposite side of the pavement, and you do get a sense of movement.

Curiously, the piece is often missed by locals and visitors because of its location high-up on the building – so add it to of your list of things to do in Cheltenham and you’ll be streets ahead of most.


Things to do in Cheltenham

Meet the Real ‘Woman in Black’

Where there’s history in a town, there are normal ghostly goings on – and Cheltenham is no different. Strange and unexplained instances have been reported in a variety of the town’s pubs, clubs and buildings.

The Bottle of Sauce in Cheltenham not only claims to be haunted by the ghost of a little boy, staff think they’ve caught the apparition on CCTV. Similarly, the Cheltenham Playhouse Theatre captured strange goings on video one evening whilst closed during lockdown. Both are worth a visit, whether you believe in ghosts or not.

Of course, the most famous of all Cheltenham’s spooks, The Cheltenham Ghost, is the town’s very own ‘woman in black’. During 1882 and 1889, in a grand Victorian house on the corner of Pittville Circus Road, the figure of a tall woman dressed in black, habitually holding a handkerchief to her face, was seen on a number of occasions by several people.

In July and August 1884, the figure was seen with increasing frequency, and by a number of witnesses. Sightings became less frequent in 1887 and faded altogether by 1889. It is one of the most well-documented hauntings on record – and was fully investigated at the time by Society for Psychical Research. The house where the hauntings took place, St. Anne’s, has today been converted into flats but you can still pass it – if you’re brave enough.

Pic credit: Pittville History


Things to do in Cheltenham

Fill Your Face with Incredible Pastries 

There are cakes, then there are the stunning pastries served at Edible Art – a new Cheltenham patisserie run by Damien Wager. Damien is primarily a self-taught pastry chef who, over the past 24 months, has risen towards the top of the U.K. pastry scene; one look at his incredible creations and you can see why.

Damien’s colourful and unique petit gateau, entremets, macarons, tarts and bonbons are more mini works of art than simple sweet treats. Each is immaculately sculpted and beautifully presented, so much so that it feels like a violation sinking your fork into one – although you try to resist doing so; it’s impossible!

Edible Art Patisserie is Damien’s first venture into a bricks and mortar business. The café is slick, clean and minimal with an ice-white backdrop that sets the sweet creations off perfectly.

Go for one of the brightly coloured treats and a hot chocolate and, whilst you’re there, check out the masterclasses on offer. They’ll take your love for pastries to a whole new plateau. Find Edible Art in Cheltenham’s elegant Montpellier Courtyard.


Things to do in Cheltenham

Shop Cheltenham’s Coolest Indie Shops

For shopping, Cheltenham has it all: the luxury boutiques where you can splash serious cash on big designer brands, the high street shops that you know, trust and love, and a plethora of independent names that’ll satisfy your quirkier tastes.

Cheltenham’s Promenade was listed by Google as one of the best shopping streets in the UK, and the town is home to one of the oldest purpose-built shopping arcades in the country – The Montpellier Arcade. Head into The Regent Arcade Shopping Centre – Cheltenham’s only under cover shopping destination – and you’ll find over 60 shops, along with Kit William’s iconic Wishing Fish Clock, which is the world’s largest mechanical clock. For independent shops, the Bath Road, the Suffolks, Tivoli and Montpellier have everything you need.

Do: Visit Catherine Colebrook’s shop in Tivoli. Catherine is the woman behind the ‘Save Water Drink Champagne’ slogan and many other cheeky creations. You can buy her bright slogan prints, colourful fabric designs and quirky homeware in her shop – but be warned; it’s almost impossible to come out empty handed.


Things to do in Cheltenham

Sup Cocktails at an Art Deco Movie Theatre

Hidden away in a leafy enclave of Cheltenham you’ll find a gem of a place, The Daffodil. Once upon a time it was a 1920s’ Art Deco cinema – the first of its kind in Cheltenham and the only cinema in the country to have ‘kissing seats’.

Today, it’s a beautiful fine dining restaurant and cocktail bar that’s been sensitively restored and refurbished by Laurence Llewellyn Bowen to thrum with its former glitz and glory.

Step inside and you’ll feel a world away from the modern age thanks to unique period features, Art Deco styling, a traditional cinema lobby cinema, golden-age projectors and a sweeping movie-star staircase that rightly takes centre stage.

Order a Hemmingway Daiquiri or a Charlie Chaplin, take a seat and soak up the glamorous atmosphere. Some other swanky Cheltenham bars worth heading to for a cocktail include Gin and Juice, Malmaison, The Ivy and The Fire Station.

Stay: If you need a base at the heart of the town’s party scene, then Cheltenham Staylets is a great option. These serviced studio apartments are slick, clean and cosy and, best of all, within walking distance of all the bars as well as the shops and parks.

Couples or friends will love the ease, comfort and convenience of Staylets – and because they’re self-catering (with fully equipped kitchens) you can eat in and make your weekend in Cheltenham even more affordable.



Things to do in Cheltenham

Laugh your Socks off at Howlers

Like every self-respecting town, Cheltenham has a lighter side to its otherwise sophisticated nature. So when it’s time for a laugh, head to Howlers Comedy Club at The Pillar Room at Cheltenham Town Hall. Known locally as ‘Howlers at the Hall’, this is a once a month comedy event that nurtures local talent and attracts comedy greats.

In 2008, Russell Kaye played here before anyone really knew who he was. Indeed, the crew behind Howlers have been booking the same acts that regularly perform at legendary venues such as The Comedy Store and Jongleurs since Feb 2007 – so you’re sure to see up-coming talent when you take your seat.

Pic Credit: Visit Cheltenham


Things to do in Cheltenham

Take the ‘Curry and Colonels’ Tour

In the 19th-century, many military officers and British Raj administrators came to Cheltenham with their families to rest, recuperate, or to retire, enjoying its pleasant climate and health-giving benefits of the waters – much-needed after the excesses of their lives in India.

As the popularity of the spa began to decline, this Anglo-Indian presence carried Cheltenham forward into a new age of prosperity, with many of the town’s finest villas and clubs built for the latest arrivals.

To this day, the influence of the Anglo-Indian link is evident in the town’s architecture and ambience and captured beautifully in the town’s wonderful Indian restaurants. On this special tour, you’ll explore the town’s connection to the East India Company and the British Raj with local tour guide, Phil, leading the way.

Do: Head out for dinner to The Mahal (which means The Palace) Indian restaurant to sample some of the flavours from that legendary era in true fine dining style. The splendid building which houses The Mahal today was itself once home to retired colonials. Then head to Memsahib Gin and Tea Bar (inspired by the British Raj period) for afternoon tea with a spicy twist.

Pic credit: Visit Cheltenham/Memsahib Gin and Tea/Mahal Restaurant 


Things to do in Cheltenham

Walk with a Hawk in the Cotswold Countryside

Well, if it was good enough for Henry VIII, then it’s a perfect thing for you to do on your Cheltenham weekend. Yes friends, Walk with Hawks is a brilliant bespoke falconry experience where you can walk with and fly some of the most beautiful birds of prey in the Cotswolds countryside.

Choose from 3 package experiences lasting from 2 – 3 hours: the Hawk Walk, the Owl Encounter or the Ultimate Experience. Each experience is run by the owners, husband and wife team, Clare and Phil Lott, who are passionate falconers, and who will teach you all about the birds, their history and the heritage of falconry in the UK.

Pic Credit: Walks With Hawks


Things to do in Cheltenham

Visit The Gustav Holst 19th Century Time Capsule 

Composer Gustav Holst was one of Cheltenham’s finest sons. Born into a musical family in the town in 1874,

Holst was a composer and music teach and is best known for his orchestral suite, The Planets – although he composed many other works during his lifetime.

You can visit Holst’s birthplace, The Birthplace Museum at 4 Clarence Road. This relatively modest Regency house has been restored and refurbished as it would have been during Gustav’s childhood here in the 1870s.

The house is a time capsule of 19th-century life with a working Victorian kitchen, Victorian bedroom, scullery and nursery. You can also experience a Regency Sitting Room, of the type popular when Cheltenham was a fashionable spa town.

One of the star attractions is the piano on which Gustav composed many of his most famous works, including, The Planets. You’ll find it in the Music Room, which contains display cabinets and information about Holst’s life and times.

Pic credit: Visit Cheltenham


Things to do in Cheltenham

Go for the Best Fish and Chips in the UK

In 2016, Simpsons Fish and Chip shop in Cheltenham was officially awarded the UK’s Independent Takeaway Fish and Chip Shop of the Year at the 2016 National Fish and Chip Awards.

Since that moment, the award-winner owners, husband and wife team Bonny and James, have been battering and frying the most delicious fish and chips in the Cotswolds.

Their secret? They believe the best fish and chips should have nothing to hide, so they don’t add salt, MSG or bulking agents to their natural batter mix. They also source the best quality fish and spuds and cook them with great care. In their chips, we trust!


Things to do in Cheltenham

Warm your cockles with local gin and ale

If real ale and local gin is your thing, then you’ll get double bubble thanks to Cheltenham’s Sibling Gin Distillery and Battledown Brewery – both based at Coxhorne Farm in Cheltenham. They have been open for 5 and 17 years respectively and are run by the same family.

Battledown Brewery was started by Roland and Stephanie Elliott-Berry and sells premium British ales and lagers, in bottles, giftsets and even ‘on draft’. Sibling Gin was founded in 2014 by Roland and Stephanie’s children: Felix, Clarice, Cicely and Digby.

Both Battledown Brewery and Sibling Gin run tours – and because the premises are right next door to one another, you can start with ale and finish with gin. Or start with gin and finish with ale. Just remember to book the taxi back into town.


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Claire Robinson Founder of Weekend Candy
Unique ideas for incredible days off
Weekend Candy showcases the most unique, creative and unusual ways to spend a weekend in the UK and Europe! Featuring brilliant experiences, quirky itineraries, inspired spaces to stay, imaginative things to do and extraordinary places to visit!
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