12 unmissable things to do in Cheltenham, May 2021

For an up to date version of the best events in May in Cheltenham head to May - What's On Cheltenham Events.

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The sun is shining, bluebells are out in force, the sound of laughter in beer gardens has returned and there are two bank holidays to look forward to this month. 

Read on for our 12 unmissable things to do in Cheltenham in May…

Enjoy the online Cheltenham Jazz Festival, 1 – 2 May 2021

Fire up the BBQ, invite a few friends over and enjoy the FREE online Cheltenham Jazz Festival hosted by Gregory Porter and Cerys Matthews this May bank holiday weekend. Watch via the Cheltenham Festivals YouTube channel here. Check out the epic line up here.

Go for a dip at the Sandford Park Lido, 1 May – 8 October

Our much loved Lido pool reopens on the 1^st May and we simply cannot wait to see locals and visitors enjoying the refreshing water once again! Bookings are being taken here.

Ride on a steam train with GWSR

It is truly wonderful to see and hear the sound of GWSR steam trains travelling through the Cheltenham countryside once again.

We experienced the new COVID-secure compartments for ourselves last weekend and we were very impressed. You travel in your ‘bubble’, embarking and disembarking at nearby Toddington Train Station. The 28-mile round trip takes you through glorious Cotwolds countryside, stopping at Cheltenham Racecourse and Broadway for a short refreshment stop and stroll along the platforms. Please note - Adults are asked to wear masks whilst on the platforms but you do not need to wear masks in your private compartment.

We 100% recommend for a fun, memorable day out.

Enjoy catching up with friends in a beer garden!

It has been genuinely heart-warming over the last couple of weeks to see friends and family reconnect and enjoy spending time together. Local beer gardens have been very popular places to hang out! Our guide to beer gardens in Cheltenham features 45+ great places to enjoy a much deserved pint or cocktail from cosy pub gardens to swanky bar terraces.

Take a walk to see the bluebells

The bluebells are out in force and it would be a crime not to see them! According to the Woodland Trust, bluebells usually flower from mid-April to late May, depending on the weather, so you have this month to enjoy them. There are lots of places in and around Cheltenham to take a bluebell walk including Leckhampton Hill, Painswick Rococo Gardens, Batsford Arboretum (Moreton-in-Marsh), Frith Wood (near Stroud) and Woodchester Park (near Stonehouse). 

Please note - At the request of the landowner of the private wood, Queens Wood in Southam, we regretably inform you that the wood has now closed to visitors due to the damage caused to the bluebells by visitors over the last two years, including the trampling over and digging up of bluebell plants (which is illegal).  

We respectfully ask that when you visit any bluebell woods visitors stick to the paths, keep dogs on leads, refrain from laying picnic blankets in the flowers, take litter home and ultimately respect the fragile nature of these beautiful flowers to protect for future generations to enjoy.  

Visit the Elephant Family at Sudeley Castle

Over 30 life-sized elephant sculptures are grazing in the grounds at our local castle, Sudeley, until the 31 May. They will then set off on an awe inspiring global migration, covering over 7,000 miles and lasting three years!

We visited on their opening day and were very taken with the magnificent wooden life-sized sculptures and the walking trail through the spectacular castle grounds. You can view our video here.

Enjoy an al fresco meal

We are very fortunate in Cheltenham, we have many fabulous places to eat outdoors from cosy gastro pubs to independently run coffee shops to some of the most popular multi chain restaurants. Why not hang up your oven gloves and treat yourself to an al fresco meal this May?

Our guide featuring 65+ places to eat outdoors in Cheltenham will provide you with lots of delicious inspiration.

Shop until you drop

Our non-essential shops are open and now is a great time to treat yourself to a new spring wardrobe. Our retailers are so happy to be back doing what they love - helping customers feel great about themselves. 

Our shopping guide features 220+ shops in Cheltenham including 60 independent boutique stores selling unique and fabulous products.

Discover the history of Cheltenham with an expert guide

Tours of our Regency town are now taking place in COVID-secure bubbles of six people. Take a walking tour with a Blue Badge Tour Guide and learn about Cheltenham’s beginnings as a one street town to Regency playground for the rich and famous. Tours can be booked through Around Cheltenham and Tour and Explore.

Enjoy a self-guided tour of Cheltenham

Prefer to do things at your own pace? That’s ok we have a tour perfect for you too! Our self-guided tour and map is free and available year round. There is also a version for kids to encourage their detective investigation skills.

Snuggle up for a night under the stars

Al fresco movies are back! Hot Fuzz is being screened outdoors at the Lido on the 21 May (followed by Dirty Dancing 24 June, Back to the Future 15 July and The Greatest Showman 12 August, all at Cowley Manor).

Hop on a bike to discover Regency Cheltenham

And last, but certainly not least. This month is the perfect time to take advantage of the fair weather and hire a bike from The Bicycle Hub (next to Cheltenham Train Station). They will kit you out with a self-guided Regency Cheltenham cycle tour which you display as an app on your phone. Cruise along the Honeybourne Line and swing by the most impressive historical buildings in Cheltenham.  Guaranteed to be a memorable day out!