The Best Things to Do in Cheltenham, Gloucestershire: Elegant Architecture, Culture, & Cotswold Charm

Cheltenham isn’t just the 'Heart of the Cotswolds', it’s a place where elegance meets everyday life. Historic streets are lined with Regency architecture. There are several leafy parks and a creative cultural scene. I’ve just spent four days there with a friend, and what struck me most was how gentle and walkable the town feels. You can wander almost everywhere on foot, from The Promenade to Montpellier, without needing to rush or hop on transport.

Visiting in autumn made it especially magical. Cheltenham is full of trees, and they were just beginning to turn: soft red, gold, and orange leaves drifting across pavements and park paths. Even the simplest stroll felt scenic, especially around Pittville Park and the quiet residential streets beyond the centre.

Another pleasant surprise was the tourist information office. The staff were genuinely friendly, offering helpful advice, maps, walking routes, and personal recommendations. These are the small touches that make travelling feel welcoming and easy.

Cheltenham is elegant, but it's also approachable, creative, and calm. Whether you're visiting for architecture, food, festivals, shopping, or just a few slow days of wandering, it’s a town that invites you to explore at your own pace.

A Short History of Cheltenham

Cheltenham began as a quiet market town, but everything changed in 1716 when natural mineral springs were discovered. Word spread quickly, and by the late 18th century, it had transformed into a fashionable spa resort visited by the aristocracy, writers, artists, and even royalty. Much of Cheltenham’s elegant character comes from this period. Grand crescents, sweeping terraces, decorative iron balconies, and columned doorways were built to impress wealthy visitors, giving the town one of the best collections of Regency architecture in England.

The Promenade, today one of Cheltenham’s most iconic streets, was laid out in the early 19th century as a leafy, dignified road for genteel strolls between the spa and the town centre. Even now, its tree-lined avenue, statues, and handsome façades reflect the elegance of that era.

Beyond the Regency townhouses, Cheltenham also has examples of Gothic Revival, Victorian villas, and Arts and Crafts homes. It is a quietly impressive architectural mix that tells the story of its growth from spa retreat to thriving cultural town.

The 10 Best Things to Do in Cheltenham

1. Explore the Montpellier District & its Regency Architecture

Cheltenham is famous for its Regency buildings, and Montpellier is one of the most beautiful areas to see them. This part of town feels refined yet relaxed with quiet streets, balconied terraces, and the unmistakable Caryatid statues guarding the shops. These distinctive sculpted female figures serve as architectural supports, taking the place of columns or pillars.

Don’t miss:

• Montpellier Gardens - owned by the borough council since 1893, these gardens are part of the Cheltenham Central Conservation Area, which, at over 600 hectares, is one of the largest in the country. The park facilities include a café, tennis courts, a play area, an arboretum with some rare trees, plenty of seating, and a bandstand that has regular concerts during the summer months.

• The Rotunda - part of the Pump Room, this domed circular room was originally used as a ballroom, and was graced by the presence of the Duke of Wellington and many of his distinguished contemporaries.

• Independent boutiques, galleries, cafés, and leafy side streets

Where to stop for coffee or lunch nearby:

• The Ivy Montpellier Brasserie — beautifully styled in one of Cheltenham's oldest spa buildings, the Ivy is perfect for afternoon tea or a leisurely lunch.

  

• Café Boho / No.131 — stylish food, cocktails, brunch, and a relaxed ambience.

• Maison Chaplais — a lovely deli and café with outdoor seating.

Montpelier is a gorgeous place to stroll slowly, window shop, and enjoy a coffee outdoors on a sunny day.

2. Wander The Promenade

Probably Cheltenham’s most recognisable boulevard, The Promenade is full of character with fountains, statues, benches, flowers, and elegant historic buildings. The wide pavements make it perfect for slow wandering, and the tree-lined stretch is especially beautiful in autumn and spring.

You’ll also find many of Cheltenham’s main shops here, from independents to familiar brands.

3. Visit Pittville Park & The Pittville Pump Room

If you enjoy parks and peaceful walks, this will likely be a highlight. Pittville Park has lakes, bridges, lawns, woodland, and quiet spots to sit and watch the world drift by. The grand Pittville Pump Room overlooks the water and is a well-preserved piece of Cheltenham’s spa-town history.

On sunny days, locals relax with ice creams or picnic blankets. It’s a restful escape just a short walk from the centre.

Try the Central Cross Café for a snack or lunch. It is right in the park, with a lovely view of the lawns

4. Enjoy Cheltenham’s Cafés, Tearooms, & Independent Food Spots

For a relatively small town, Cheltenham has a big food scene. You’ll find:

• artisan bakeries

• cosy tearooms

• creative brunch cafés

• restaurants celebrating local produce

If you love lingering over good coffee or hunting down homemade cakes, you’ll feel right at home.

5. Experience Cheltenham’s Festivals

Cheltenham has a vibrant festival calendar and is famous for its cultural events. If you’re visiting at the right time of year, the town comes alive with performances, workshops, live music, talks, and street entertainment. The main festivals usually fall around these dates:

• Cheltenham Jazz Festival — late April to early May

• Cheltenham Science Festival — early June

• Cheltenham Music Festival — early July

• Cheltenham Literature Festival — early to mid-October

• Cheltenham Races (The Festival & Gold Cup) — mid-March

Dates vary slightly each year, so it’s a good idea to check the official festival websites if you’re planning a trip around an event. Accommodation can book up early during festival season, so booking ahead helps.

6. Shop Independent in The Suffolks & Bath Road

If you enjoy browsing local makers, vintage finds, gifts, antiques, or one-of-a-kind pieces, head to The Suffolks and Bath Road. These neighbourhoods feel lived-in and local with colourful shopfronts, small cafés, friendly owners, and creative businesses.

It’s the ideal contrast to the grand architecture of the town centre.

We stayed in a private rental property in this area. It was the perfect location with lots of shops and eateries, but still within easy walking distance of the town centre.

7. Take a Day Trip Into the Cotswolds

One of the joys of basing yourself in Cheltenham is how easy it is to explore the nearby Cotswolds, where you will find a patchwork of stone villages, gentle river walks, and timeless market towns. We managed to visit several during our trip, each with its own charm and character.

Bourton-on-the-Water - we arrived at dusk, just as the soft evening lights began reflecting in the River Windrush. It was a beautiful, almost storybook moment with the water sparkling under the little footbridges. It was easily the busiest place we visited in the Cotswolds; while other villages had been quiet or even deserted earlier in the day, Bourton was still packed with visitors wandering the riverside and gathering around the cafés and shops. Even with the crowds, there was something charming about seeing the village come alive at twilight, its stone cottages and gentle river looking especially pretty in the fading light.

Stow-on-the-Wold - one of the Cotswolds’ highest and most historic market towns, known for its wide market square, honey-coloured stone buildings, and charming independent shops. It has a relaxed, unhurried feel, and the medieval lanes leading off the square are full of cosy cafés, boutiques, and antiques. Even if you’re just passing through, it’s the kind of place where a gentle wander and a warm drink make a perfect hour or two.

Upper and Lower Slaughter - we visited both of these. They are two of the most picturesque villages in the Cotswolds. Lower Slaughter is very small, with just a handful of cottages and its peaceful millstream. When we arrived, it was wet and quiet with not much happening. It was atmospheric in its own way, but easy to explore in just a few minutes. Upper Slaughter, on the other hand, felt instantly charming. Even in the rain, it was beautiful to walk along the water, with little stone bridges and pretty houses tucked along the lane. On a dry day, the walk between the two villages would have been lovely, but with the weather against us, we went in Bertha (my campervan 😊) instead. Even so, both villages had their own quiet charm, and Upper Slaughter in particular really stayed with us.

Broadway & Broadway Tower - often called the “Jewel of the Cotswolds,” Broadway is a picture-perfect village with a long, elegant high street lined with traditional stone cottages, galleries, and tearooms. It’s an easy place to stroll, browse, and linger. The nearby Broadway Tower is one of the area’s most iconic viewpoints, offering sweeping countryside scenery. It was a regular haunt of mine when I was working in nearby Chipping Campden over 40 years ago, but that's a story for another day 😂. Whether you’re exploring the shops or just soaking in the atmosphere, Broadway feels timeless and beautifully kept.

Winchcombe & Sudeley Castle - we really enjoyed Winchcombe, even though the weather was dreadful. It rained steadily for most of our visit, but there was still something incredibly atmospheric about the Tudor buildings, timber-framed fronts, and narrow side streets glistening in the wet. The local museum was a highlight. It was far more interesting than we expected, full of fascinating details about local history and the surrounding landscape. Despite the downpour, Winchcombe felt welcoming, full of character, and like the kind of place we’d love to return to on a sunnier day to explore the countryside walks between the villages. We didn't visit Sudeley Castle on this occasion, but I remember going there years ago, and it's definitely worth a look if you have time.

Tewkesbury - another highlight of our time in the Cotswolds, so much so that it warrants a blogpost of its own 😊. Click here to read it.

8. Relax in Sandford Park & the Lido

Sandford Parks Lido is a beautiful outdoor swimming pool in the warmer months, surrounded by gardens, water features, and quiet spaces to sit. Even without swimming, Sandford Park itself is perfect for gentle walks and photography, especially when flowers are in bloom.

9. Discover Cheltenham’s Street Art

Cheltenham isn’t only about elegant Regency buildings; it has a modern, creative side too. The town hosts the annual Cheltenham Paint Festival, which has helped transform walls, alleyways, and unexpected corners into a colourful outdoor gallery. As you walk, you’ll spot large-scale murals, smaller hidden pieces, and even sculptural artworks tucked along pavements and public spaces. Some pieces are bold and eye-catching, others quietly blend into the urban landscape, so wandering becomes a bit of a treasure hunt. It’s a lovely way to see a different side of Cheltenham, and a great contrast to its formal architecture - proof that the town continues to evolve while celebrating creativity.

10. Visit The Holst Victorian House

The birthplace of composer Gustav Holst is now a small, atmospheric museum. It’s a quieter attraction, but beautifully preserved and full of interesting history, especially if you enjoy music or Victorian life.

Where to Stay in Cheltenham

Cheltenham offers a diverse range of accommodation, including hotels, boutique stays, and apartments, most of which are within easy walking distance of the main attractions.

Recommended accommodation:

• No.131 — elegant Regency townhouse with bar and restaurant

  

• Queens Hotel — grand, historic, and right by The Promenade

  

• Hotel du Vin — stylish and central

  

• The George — modern, comfortable, great location

  

For budget-friendly stays, town-centre apartments and guesthouses in Pittville or Montpellier are excellent options.

Did You Know? Cheltenham Edition

• 💧 Cheltenham became famous because of its mineral springs. The first spring was discovered in 1716, turning a quiet market town into a fashionable spa resort for the wealthy and aristocratic.

• 👑 A king helped put it on the map. King George III visited in 1788 to “take the waters,” and Cheltenham’s popularity instantly boomed.

• 🌳 The Promenade was built for elegant strolling. Created in the early 1800s, it was designed as a tree-lined avenue for visitors to wander between spa buildings and shops.

• 🏛 Cheltenham is a showcase of Regency architecture. Grand crescents, sweeping terraces, balconies, ironwork, and columned entrances were built to impress spa visitors.

• 🎨 Not just historic — it’s creative. Cheltenham now has one of the biggest street art festivals in the UK, adding colour and modern personality to a town once known only for elegance.

• 🎶 A composer was born here. Gustav Holst, the composer of The Planets, was born in Cheltenham, and his childhood home is now a museum.

A Perfect Destination for Slow Travel

Cheltenham is the kind of place where the best memories come from simple moments like sitting on a park bench with a coffee, watching leaves fall across a pavement, discovering a local shop, or chatting with a helpful local at the tourist office.

It’s grand but gentle, historic but creative, and full of life without feeling crowded. Whether you’re visiting for a weekend or using it as a base to explore the Cotswolds, it offers that rare thing in travel - the space to slow down, wander, and enjoy.

Watch this Video to Learn more about Cheltenham

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