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Right up there with some of the best experiences in England that you can possibly have, is a day trip or weekend break to Cheltenham. Most famed for its stunning Regency architecture, action-packed festivals and horse-racing, there are so many fun things to do in Cheltenham.

But first, a few more words about the town itself.

It was once the place to be in the 18th century after its spa waters were discovered and commercialised. Wealthy Londoners saw it as the perfect place to escape the hustle and bustle (and smog!) of the capital.

Nowadays, the stunning stucco facades and ripe history are blended with the modern including a newly established street art scene. With this blend of the new and the old in mind, here are a few of my favourite and most fun things to do in Cheltenham.

1. Explore all of the beautiful parks and gardens

Imperial Gardens

Cheltenham is often known for its architecture and stunning buildings, but did you know that the town also has over 600 acres of parks and gardens for you to explore? In fact, it’s often called ‘The Garden Town of England’!

The Imperial Gardens are found close to the town’s centre where all the great shopping is, which means you have a superb little rest stop in between browsing all of Cheltenham’s best stores or when marvelling at the beautiful Regency architecture.

Pittville Park, on the other hand, really does steal the show when it comes to parks and gardens in Cheltenham. It’s the largest park in the town, which means there’s loads to see here including a canal, lake, myriad of cafes and tea rooms, as well as Pittville Pump Room, which houses the spa waters that really helped to put Cheltenham on the map in the 18th century.

Other notable parks and gardens in Cheltenham include Sandford Park, complete with lido nearby, and Montpellier Gardens, which is often home to Cheltenham’s vast array of festivals.

Read more about Cheltenham’s parks and gardens in this blog post >>>

2. Go on a bike ride following the Regency Cycle Trail

Although Cheltenham is quite a small town, so exploring on foot is fine to do, if you’re limited for time, then the easiest way for you to see everything is with a scenic bike ride.

For as little as £20, you can rent bikes near to the train station from The Bicycle Hub — they’ll even throw in access to their phone app and an information pack that both contain details on the route you should follow (the Regency Cheltenham Cycle Trail) and other top sights you may want to check out.

And the best bit? Access to this app and info pack is yours to keep after your day of bike riding is over!

Some of my favourite sites along the cycle trail are:

For those of you with young children or anyone who is a little wobbly on a bike (like me!), this trail is a great option as it does make the most of the town’s off-road cycle paths. Just note that some of the trail is along roads, so you may want to either skip those parts and come back to them later, or just walk along with your bike for a bit.

3. Scout out some traditional Regency architecture

Even though there is a lot to see and do in Cheltenham, there’s no escaping the fact that Cheltenham is the most complete Regency town in the UK.

So if stunning 18th century architecture is your bag, then Cheltenham is (by far) one of the best places to visit.

To see the best of the Regency architecture on offer in Cheltenham, I recommend you head to:

  • Pittville Park – to photograph the Pittville Pump Room (NB: at the moment, there are some renovation works being done to the roof so don’t expect Insta-worthy photos of every angle of the pump room for the time being)
  • Montpellier Walk – look out for the Caryatids (modelled on the Acropolis in Athens), which can be seen on the sides of each shop
  • The Municipal Offices – alongside the stunning architecture, keep your eyes peeled for The Neptune Fountain (inspired by the Trevi Fountain in Rome)
  • Imperial Square – walk to the end of this street and take a few moments to admire the Imperial Fountain; it’s a bit of a hidden gem within Cheltenham as it’s hidden from view from most of the passing roads and streets!

Learn more about Cheltenham’s Regency architecture in this blog post >>>

4. Hunt for some interesting street art

Street art in Cheltenham

Hunting for street art is probably not the first thing that springs to mind when looking for things to do in Cheltenham.

But did you know that Cheltenham is home to a street art festival called PaintFest?

Following the success of the festival last year, in September of this year, 120 artists were asked to bring their creative flair to various buildings, walls and other surfaces throughout Cheltenham in a bid to show more diversity and an extra layer of fun within the city.

As it stands, this festival should be happening again next year. But the best part about it being a street art festival is that the finished pieces are on display throughout the year.

There is a 6km walk you can follow to see all of the street art locations, but in case you don’t have time for the full walk, here are a couple of top locations you should head straight for:

  • The Brewery Quarter – the geographic centre of 2018’s festival
  • Williams Cycles – showcasing work from over half a dozen different artists
  • The Honeybourne Line – two tunnels and four bridges make way for colour!

5. Have a fine dining experience in a posh restaurant

Cheltenham is home to much fine dining, but by far the finest, would be either Ivy Brasserie or The Daffodil.

The Ivy Brasserie can be found in the stunning rotunda building towards the top of Montpellier, which means dining here often involves gazing up at the domed glass ceiling in between mouthfuls.

The Daffodil is housed inside what was once a cinema in the 1920s. The Art Deco feel has never once been lost inside this posh restaurant and accompanying bar area, which is complete with a grand sweeping staircase on each side of the restaurant.

Bonus #1: Attend a fun and free festival

Cheltenham Literature Festival

One thing Cheltenham seems to be rather infamous for is its festival calendar, so if your visit coincides with one of these superb events, then you’re in for a real treat:

Each festival has various free events and shows you can attend, while others are paid for and can be booked in advance.

So whether you’re into music, science, books or street art, you’re sure to find something you love!

Bonus #2: Stay at the Cotswold Grange Hotel

Dining Room at Cotswold Grange Hotel, Cheltenham

During our visit, we were lucky enough to sample some of the menu and get a tour of the rooms at the Cotswold Grange Hotel.

Without a doubt, this was one of the most spectacularly decorated hotels I’ve seen in a long time. Cotswold Grange is an independently-run boutique hotel that is housed inside an 18th century period building and has been lavishly restored and decorated by the owners and local artists.

If you’re anything like me, then you’ll be particularly enamoured with the dining area, which has ornate mirrors and gold-flecked bird illustrations on all of the walls, as well as a central masterpiece of golden elephants.

The guest rooms themselves are all spacious with en-suites; one suite even had a freestanding bath tub inside it! The prices per night are pretty great for what you’re getting, so would suit any mid-range budget just fine.

But it’s the finishing touches that always get me! At Cotswold Grange, they’re able to tailor the room setup to your needs. So whether you’re travelling as a couple, with a baby, young children, or even teenagers, you should be well catered for.

And those with dogs? Yep, you’re welcome too. There are 2-3 rooms on each floor that allow for dogs, hurrah!

With all this said, if you’re looking for a charming quintessentially Regency experience, then this is the hotel for you!

Book your stay at Cotswold Grange Hotel via Hotels.com here >>>

Bedroom Suite at Cotswold Grange Hotel, Cheltenham


Well, there you have it… my recommendations for some of the best and most fun things to do in Cheltenham. What are you most excited to do first? Let me know in the comments…

Feeling inspired? Share the wanderlust around!

Totally Honest Disclaimer:
Visit Cheltenham kindly invited me for a day out in Cheltenham in partnership with them and their sponsors: The Bicycle Hub and Cotswold Grange Hotel. As always, all thoughts, opinions, words and photos are my own… this was genuinely a superb day out! This post also contains affiliate links — if you happen to book something via one of these links, I’ll receive a little bit of commission at absolutely no extra cost to you.

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