The Ultimate Guide to Cheltenham

The Ultimate Guide to Cheltenham

As a born and bred Cheltonian, I feel like it’s only fair I give my hometown of Cheltenham some airtime on my blog, particularly when I’m feeling a little homesick. The town is a blend of festivals, arts, beautiful scenery, and fun, all mixed together with a splash of occasional pomp, pageantry, and the odd celebrity chucked in for good measure. Having spent the best part of my life living in Cheltenham, here’s the lowdown on everything you need to know about the UK’s most fabulous spa town.

A row of terraced houses in Imperial Gardens, Cheltenham
Imperial Gardens, Cheltenham

Where is Cheltenham?

Cheltenham is branded ‘the heart of the Cotswolds’, a vast area of rolling countryside and natural beauty in south-west England, stretching from the Severn Valley to the upper Thames, that also happens to be the second largest protected landscape in England after the Lake District. With a humble population of 120,000, the Gloucestershire town is famous for its Regency architecture, having risen to fame as a health and holiday resort since the discovery of its mineral spa waters in the early eighteenth century. Today, the town remains a tranquil retreat for thousands of city slickers seeking a break from the hustle and bustle of life in the Cotswold countryside, with London just a cool 88 miles away down the A40 and Birmingham within reach just under half of that distance.

Exploring rural Prestbury, Cheltenham
Exploring the suburbs around Cheltenham

Why visit Cheltenham?

Firstly, it’s a beautiful town that preserves some wonderful heritage and architecture. It seems as though every corner you turn, you’ll see a beautiful row of perfectly symmetrical terraced houses, whether it’s the famous Royal Crescent or a more residential area. With parks scattered across the town, fountains, sculptures, and rainbow coloured flowerbeds and hanging baskets in every nook and cranny, it’s little surprise Cheltenham has been a regular winner of awards as a garden town. With countryside within easy reach of the town centre, visitors can choose one of many walks to experience breathtaking views of the town and beyond across the countryside.

Another reason to visit is the town’s plentiful festivals – whether literature, jazz, cricket, horse racing, science, art or even gin is your thing, Cheltenham boasts some of the most widely recognised meets in the world. Each year, the Cheltenham Festival grows to attract a larger group of punters trying their luck on the horses at the infamous racecourse, bringing along royalty and celebrities from across the nation. The much celebrated Times Literature Festival most recently featured names including Hillary Clinton, Russell Brand, and Nigella Lawson amongst other huge literary names.

Views from the Panoramic Restaurant, Cheltenham Racecourse
Cheltenham Racecourse

Aside from its surroundings and festivals, the town offers some wonderful places to stay with a growing number of chic establishments opening up every month and filling the lifestyle columns of national newspapers. There’s cuisine for all tastes, from some of the most delicious pub grub you’ll find in this part of the country to Michelin star fine dining for those craving something a little fancier. And for those looking to shop in the day and mingle over a martini in the evening, Cheltenham’s plethora of boutique bars and independent shops will more than satisfy. Nearby attractions include the world-famous Cotswold villages of Bourton-on-the-Water and Bibury, impressive historical buildings including castles and cathedrals, the Romanesque and Gothic city of Gloucester, plenty of countryside retreats and spas, and for larger city breaks, Oxford, Birmingham, and Bristol can all be reached within an hour’s travel time.

When is best to visit Cheltenham?

You won’t regret visiting the town in summer, when the leafy Promenade is dappled with sunlight, causing the smiles of locals to be just that little bit bigger than usual. You can expect to see gaggles of shoppers enjoying an al fresco French meal, and the young and beautiful saying cheers over a cocktail or two in the Montpellier region of the town. Spring is also a great time to visit thanks to the blossom and daffodils that crop up on every street, and Christmas is a particularly pretty time to visit thanks to the town’s impressive festive decorations and great choice of shops and dining options.

Of course, Cheltenham is bustling throughout the year thanks to its regular horse racing meets, so it’s worth taking a look at when these are throughout the winter and spring months. The Gold Cup Festival runs each year in the week of March closest to St. Patrick’s Day, bringing the town’s most vibrant week of the year when revelry, pints of Guinness, and all-day breakfasts don’t falter in their force or volume. Other key events throughout the year include the Science and Food and Drink Festivals in June, the Cricket Festival in July, and the Literature Festival in October, so be sure to take a look at what tickles your fancy before you book your visit. Don’t also miss the quirky, world-renowned Cheese Rolling event which takes place on Cooper’s Hill every May – brave contestants try their chances at catching a cheese that’s plummeted down one of the town’s steepest hills.


Where is best to stay in Cheltenham?

The town has a number of gorgeous boutique hotels to accommodate for a range of guests. Here are a few of Cheltenham’s top hotel picks:

Ellenborough Park

Let’s skip to exactly why Ellenborough Park is repeatedly considered one of the finest places to stay in Cheltenham:

  • A spa with 7 treatment rooms
  • A boot room, with a choice of Dubarry and Hunter boots, all colours of the rainbow
  • An outdoor pool that’s kept at a soothing 30 degrees no matter which time of year
  • Telescopes for watching the horse racing at Cheltenham Racecourse
  • The Restaurant, with original Tudor fireplaces and stained glass windows
  • 90 acres of beautiful leafy land
Ellenborough Park, Cheltenham
Ellenborough Park

No 131

With a great central location on Cheltenham’s famously fabulous Promenade, here’s exactly what’s so great about Hotel No 131:

  • Enormous beds and deep roll-top Victorian baths
  • Each room is uniquely and elegantly decorated
  • A gorgeous Georgian dining room with an art deco makeover
  • Its deliciously trendy cocktail bar, Crazy Eights
  • Located on beautiful Imperial Gardens

Cowley Manor

As a wonderful estate on acres of land in the Cotswolds countryside, Cowley Manor boasts a number of enviable features:

  • 55 acres of beautiful countryside land
  • A stylish indoor and outdoor pool with a bar, heated all year round
  • The C-Side spa with four treatment rooms
  • Fitness classes including yoga and bootcamp sessions
  • A CD and DVD library
  • The gorgeous oak-panelled dining room, serving up delicious dishes

Where are the best places to live in Cheltenham?

If your exploration of Cheltenham is a little more permanent, you’re in luck. It’s a great town to live in for those looking for a relaxed and enjoyable lifestyle, with great shopping, attractions, restaurants and bars on your doorstep. For families, there are plenty of good schools and things to do, and it was actually regarded by the Telegraph as the best place in the UK to raise a family. With a great location that’s within easy reach of many of the country’s top cities, it’s also a very convenient place to live, and Cheltenham has recently seen the highest house price increase in the UK thanks to its desirability, ensuring you it’s a worthwhile place to reside.

Here are some of the top areas to live:


Famed for being one of the more glamorous areas of Cheltenham, Montpellier is at the south end of the town’s famous leafy Promenade. Dating back to the early nineteenth century thanks to its history as the destination when visiting for the town’s spa, it’s since been a hub for boutique restaurants, cafes, independent shops, and bars. Although it can top the higher end of the town’s price scale, there is a stunning range of historic apartments and townhouses.

Montpellier Gardens


Home to the renowned Pump Rooms and Cheltenham’s largest park and lakes, it’s a great place to relax with a leisurely walk and a coffee, catch a game of tennis or to take the family. With plenty of green areas, it’s a pretty part of town to live and within close proximity of the town centre. Expect to find large townhouses and beautiful Regency apartments in this area of Cheltenham, many with great views across the park.


With many of its stunning architecture listed, you’ll find some particularly nice estate in this region of town, developed by two families back in the eighteenth century. Just a short walk from the boutique area of Montpellier and the town centre, it’s well positioned for a very comfortable lifestyle and is one of the most desirable areas of Cheltenham. There are plenty of stylish townhouses and luxury flats in this area that are certainly worth a look.


A little further out of town is the historic village of Prestbury. Strangely known as being the most haunted village in the UK thanks to its reported frequent visits from the Black Abbot, you’ll find buildings from all eras here – from Tudor to Gothic, to the present day. With a handful of great pubs serving a decent pint and grub, it’s also situated just down the hill from Cheltenham’s iconic racecourse and plenty of countryside for some lovely walks at the weekends. You’ll find larger family homes here, to tiny thatched cottages – there’s quite the range!

Sheep in the fields near Prestbury, Cheltenham
A view to Prestbury

What to see and do in Cheltenham

There’s plenty to keep you occupied in Cheltenham, no matter your age, tastes, or preferences. Here we’ve rounded up the top attractions you simply can’t afford to miss:

Enjoy the sunshine outside

Cheltenham is a beautiful garden town, and one of the best things to do is meander around a park with a coffee after lunch, taking in the sights from flowerbeds to fountains. Some of the best parks include The Park, Montpellier Gardens, Imperial Gardens, and Pittville Park. The town’s famous Sanford Park Lido is also open from April until September and is perfect for a refreshing dip outdoors. In the summer, you’ll be joined by plenty of others enjoying the sunshine so don’t forget your snacks and a bottle of bubbly – cheers!

Wine and pizza in Imperial Gardens, Cheltenham
Enjoying the sun in Imperial Gardens

Enjoy a little history

The town is steeped in history, so make sure to visit some of its fascinating buildings. Sudeley Castle is certainly worth a visit thanks to its beauty and historical significance. Boasting royal connections back over a thousand years, it’s also the burial place of Katherine Parr, Henry VIII’s last wife. A visit to Pittville Pump Rooms will uncover plenty of the town’s history, as an iconic Regency building, it overlooks the majestic grounds and lakes of Pittville Park. Don’t forget to taste the spa waters that made Cheltenham so famous – despite their interesting taste, it was believed that they would cure any illness.

Find your diamond in the rough

Join in one of the world’s most luxurious treasure hunts thanks to Cheltenham’s Beards Jewellers, which joins forces with Maggie’s Cancer Care each April to deliver the Beards Diamond Rush. Ten diamonds each worth thousands of pounds are hidden all over the town with just a treasure map and volunteers selling clues for guidance. Whoever discovers the diamonds gets to keep them, so bring your best detective skills! It’s great fun, and for an even better cause.

Visit the local landmarks

Despite being a relatively small town, Cheltenham has a number of key (and occasionally quirky) landmarks. Firstly, take a look at the controversial Hare and the Minotaur statue on the Promenade which is created from scrap metal by Gloucestershire-based artist, Sophie Ryder. If you head up to Montpellier, you’ll see Regency sculptures in the shape of the Caryatids that adorn the shop facades of the area, based on originals from Athens’ Acropolis. Other key sights include Neptune’s Fountain on the Promenade, rumoured to be a nod to Rome’s Trevi Fountain, GCHQ (Government Communications Headquarters) which is fondly known locally as ‘The Doughnut’ thanks to its unique shape, the iconic Municipal Offices, beautiful Town Hall, and of course, Cheltenham Racecourse in Prestbury Park.

Pitville Pump Rooms reflecting on the lake at dusk
Pittville Pump Rooms

Go to a festival

No matter what time of year you visit Cheltenham, there’s bound to be a festival somewhere in the calendar. If sports are your thing, check out the Gold Cup Festival for some of the best horse racing in the world, or if you’re more into cricket, the Cheltenham Cricket Festival at Cheltenham College is one of the town’s most civilised sporting events. For the foodies, the annual Cheltenham Food & Drink Festival lands in Montpellier in June, the Wine Festival in April, and the new Gin Festival in July shouldn’t be missed for a truly British experience! For those seeking a little more culture, the world-famous Cheltenham Literature Festival takes place in October, the Jazz Festival in May, and the Science Festival in July.

Indulge in some retail therapy

Cheltenham has always had a healthy offering of retailers to satisfy shoppers, with visitors from all over the nation visiting for some retail therapy – it even made it into Savill’s top 10 towns for high street retail investment. Head to the pedestrianised High Street for all the usual major chain stores, as well as the Regent Arcade for some undercover shopping with over 60 stores and cafes. This year will also see the opening of John Lewis, neatly adding another string to Cheltenham’s bow. The Promenade is a beautiful leafy boulevard that is the home of great major stores and al fresco dining, and at the end, Montpellier features some elegant boutique stores, wine bars, and cafes in one of the town’s most sophisticated areas. Don’t miss The Suffolks if you’re in search of specialist and antique shops, as well as Tivoli and Bath Road for independent shops and a community spirit – as well as a spot of lunch.

Go for a country walk

Thanks to its beautiful location in the heart of the Cotswolds, as you can imagine there are plenty of scenic trails and walks that can be taken in and around Cheltenham. One of the most popular routes is the climb up Cleeve Hill, Gloucestershire’s highest point, which offers some spectacular panoramic views across the county. Other great walks include hiking up to the Devil’s Chimney on Leckhampton Hill, and the famous Cotswold Way. No walk would be complete without at least one stop to one of the beautiful countryside pubs en route or at the end of a busy day of walking – don’t miss the Rising Sun on Cleeve Hill for a pint with a view, and the very beautiful Mill Inn in Withington.

Panoramic views across Cheltenham from Cleeve Hill
Views from Cleeve Hill

Get cultured

As a town priding itself on its strong history of arts, culture, and music, it’s little surprise that there are some great opportunities for learning plenty and seeing a number of exhibitions. First up, stop off at The Wilson for coffee and cake, before exploring the intriguing museum with its collection of arts and crafts, fine art, and incredible archives that uncover the town’s history and people. For classical music fans, head to The Holst Birthplace Museum which is dedicated to the famous composer, Holst, who is best known for his work on The Planets. If you’re keen to catch a theatre production, the beautiful Everyman Theatre is intricately and beautifully designed and features many ballet, opera, drama, dance, comedy, and musical productions, as well as traditional pantomime.

What’s nearby?

Cheltenham has a great central location, which means it’s near to plenty of other exciting places and attractions:

  • The Cotswolds – plenty of other beautiful towns and villages are within easy reach for walks, lunch, and shopping. Don’t miss Cirencester, Bourton-on-the-Water, Stow-on-the-Wold and Bibury, and stop for a bite to eat at Daylesford Farm. Within an hour, you can reach the Oxfordshire countryside which is equally as beautiful – explore the spires of the university city of Oxford, mooch around the quaint town of Witney, and if you’re a member of the arts, head to the luxurious spot of Soho Farmhouse at Chipping Norton.
  • Great cities – Gloucester is just ten miles down the road from Cheltenham, and boasts one of the most magnificent cathedrals you’ll ever see. Wonder the historic streets, and be sure to catch the ‘cherry and whites’ at a game at Gloucester Rugby Stadium. The larger cities of Bristol, Birmingham, and Cardiff can also be reached within around an hour.
  • London – is well connected to Cheltenham, with plenty of trains, coaches, and buses each day. London Victoria and Paddington stations can be reached within two hours making it accessible for a day trip, and the major airports can be easily connected to from there.
Cleeve Hill

Which celebrities live in Cheltenham?

Despite being a relatively small town, Cheltenham has a few claims to fame:

  • Birthplace of Brian Jones, founder of the Rolling Stones
  • Gustav Holst, composer of The Planets, was born and raised in the town
  • Alice in Wonderland author, Lewis Carroll, was said to base his famous story on a mirror in a Cheltenham house he was staying in
  • Local celebrities include ex-X Factor presenter, Kate Thornton, Shaun of the Dead actor, Simon Pegg, chick-lit novelist, Jilly Cooper, as well as royalty in the shape of Zara Phillips and Mike Tindall
  • It’s a hotspot for celebrities seeking a countryside retreat, with Kate Moss, Damien Hirst, Hugh Grant, Lily Allen, and Kate Winslet all owning properties around Cheltenham

Getting around

It depends on where you choose to stay in Cheltenham, but typically you’ll need a car if you’d like to explore the town and its surrounding areas a little more. If you’re staying in the town centre, walking will most likely suffice, particularly in the summer months. Transport connections, are however, pretty regular with bus services, taxis, and trains.

Where to eat in Cheltenham

Cheltenham has a great, blossoming dining scene that shows no signs of slowing down. There’s something for everyone, with a great crowd of delicious gastro pubs to highly commended brunch spots, to Michelin star dining. Here are a few of the best:

  • The Ivy – the new kid on the block, this world-renown London export landed in Cheltenham last autumn and has been blowing the town’s socks off with its delicious, fancy fare. It’s worth a visit just for the beautiful Rotunda building it’s situated in, and serves up delicious cocktails and gourmet dishes from lobster to steak, and a delicious all-day brunch.
  • The Bottle of Sauce – this gastro-pub was a welcome addition to the Cheltenham foodie scene, serving up delicious burgers, pizzas, and bowls to satisfy the palate. Offering a trendy social space where you can even play a game of ping pong, it’s a good place for good grub.
  • The Fire Station – appearing on the scene a few years ago as a renovated fire station, it has a beautiful interior and developed a great reputation for its bottomless brunch, the first of its kind in Cheltenham. It’s a great spot for after-work drinks or a delicious three-course meal, with a great ambience for dinner with friends or a date.
  • The Daffodil – a Cheltenham classic, this beautiful Art Deco building and ex-cinema serves up reliably fantastic, quintessential British dishes in gorgeous surroundings. Don’t miss out on their tasty roast dinners or fillet steak with peppercorn sauce, you won’t regret it!
  • Le Champignon Sauvage – one for a classier occasion, this is Cheltenham’s only two Michelin star ranked restaurant. Described as modern French with a unique touch, it’s reputation precedes itself as arguably the finest place to eat in town.
Shakshuka at The Fire Station, Cheltenham
A shakshuka brunch at The Fire Station

Where to drink in Cheltenham

Cheltenham recently gained a reputation as the coffee capital of the UK, having boasted the highest number of coffee shops per square foot. With no shortage of watering holes in this town either, it’s pretty apparent Cheltonians enjoy a good drink. Here are a few of the best:

  • The Coffee Dispensary – serving up speciality coffee, this is one of Cheltenham’s most popular coffee spots, and for good reason. Choose your desired blend from across the world, and the helpful staff will help advise you on a coffee if you’re unsure.
  • The Retreat – known across the town for its great atmosphere, events, and iconic red walls, The Retreat is a hotspot for young and beautiful locals and celebrities alike. Enjoy a glass of something cold in its summer patio, or huddle in and make new friends in the winter months.
  • Crazy Eights – as the cocktail bar of the elegant No 131 hotel overlooking Cheltenham’s Promenade, you know you can expect something fabulous from this bar. With beautiful interiors and a glass roof, Crazy Eights features an extensive cocktail list that will keep you wanting more.
  • John Gordon’s – this bar is what can only be described as a ‘gin library’ with rows of unique and fancy gin bottles with a sliding ladder to reach them. With friendly locals and extremely knowledgeable staff, you’re guaranteed to discover a delicious drink that you’ll love.
  • Montpellier Wine Bar – an old time favourite and located in the stylish area of Montpellier, this classic bar offers al fresco socialising, and an innovative wine list. If you’re after something with a few more bubbles, the extensive champagne and prosecco menu will help you get your fix.
A cuppa at a Cotswold pub

Is there anything I’ve missed from my guide to Cheltenham? Let me know if there’s something you’d include!

Follow me:

Instagram (@lkemp91)

Twitter (@L_E_Kemp)

Pinterest (@lxk978)


I’m Laura, a roaming blonde who recently made the leap from my home in the Cotswolds, UK to be based across the pond in Vancouver, BC for a brand new job and plenty of adventures.

Find me on: Web

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.