There are 11 stops in total, we expect the trail to take around an hour to walk, but feel free to stop at some of the locations along the way to discover more! You can visit the stops in any order, but the order below is our recommended route.
Each location has an initial clue to find it as well as a photo but if you’re stuck you can use the hint drop downs, which also include map links to each location. Most answers can be found around the location, and there’s an additional hint in the drop downs, but feel free to do extra research if need to.
Stop 1:
The first stop on the trail is where you might already be! If not, make sure you come to collect your answer sheet.
You might be able to find the address somewhere on this website!
Map link
Question: Which ‘secret’ Cheltenham resident is Operation Foresight based on?
This Government’s current office is known as ‘The Donut’ and houses the original Enigma machine used to break German code during the war.
Stop 2:
This location, originally opened in 1891, is one of the oldest existing auditoriums of its designer
It’s name indicates that its ‘A Theatre for all’
Map link
Question: What is the name of the designer?
You can find his name on a blue plaque above the entrance doors
Stop 3:
This location commemorates ‘The men of Cheltenham who gave their lives for you in the Great War’
This stands proud outside the Municipal Offices
Map link
Question: In 2014 six new names were added, one being the only woman to appear on the memorial. What was her name?
With 1297 names in total, it might be best to google this one!
Stop 4:
You might think you’ve been transported to Rome, but don’t worry we’re still in Cheltenham!
Head from the previous stop up towards the big wheel and you should spot this one on your right
Map link
Question: What is the name of this location’s designer?
There’s an information board close by that tells you everything you need to know!
Stop 5:
Known as ‘Caryatids’, these lovely ladies date back to 1840 and adorn the shops and restaurants in this location.
Continue in the direction you were walking from the previous two stops and the first ones you should see will be surrounding Ask Italian
Map link
Question: How many are there in total? See if you can count them all!
From the front of Ask Italian, walk up its right hand side to find the rest. Don’t forget to look back on yourself too!
Stop 6:
This location was founded in 1853 with the goal of providing “a sound academic education for girls”.
A short walk back towards town from the previous location, this is one of the most prestigious girls schools in the UK
Map link
Question: What was the name of the first principal, living and working here for nearly 50 years?
with many buildings and vast grounds, you might need to walk around the perimeter until you find this blue plaque
Stop 7:
One of our favourite free activities to do in Cheltenham, this location was named after Cheltenham born scientist and explorer Edward Wilson, who sadly lost his life on his expedition to the South Pole.
This location is Cheltenham’s main art gallery
Map link
Question: Not only did he conduct extensive scientific research during the expedition, Wilson also produced over 100 drawings and ____________, some of which can still be found in the Open Archive.
As well as his sketches, Wilson painted sceneries and animals in a specific medium
Stop 8:
Head back towards the town centre for this next location. Opened in 1806, this jewellers was one of the first registered limited companies in the UK.
All though currently surrounded by scaffolding, you should still be able to spot their purple signage
Map link
Question: What were these jewellers commissioned to make the first of, still continuing to make them annually to this day?
You might not find the answer at the shop (unless you ask someone!) but the event it was made for sees around 250,000 visitors to Cheltenham every March
Stop 9:
A hidden gem of Cheltenham: home to a world renowned composer and now a museum you can step inside! (we encourage you to visit but the museum does have an entrance fee, you don’t need to go in to answer this question)
You’ll find this location around the Pittville area, look out for the green keyhole logo!
Map link
Question: What is the name of the famous Cheltonian born here?
His name can be found on the white plaque next to the door
Stop 10:
Very close to the previous stop, this location is also known as Cheltenham’s ‘Grand Entrance’
Walking out the Holst Victorian House, just look to your right and you should see it!
Map link
Question: What can be seen atop the gate, said to be the first to discover Cheltenham’s spa waters?
have a look at the gate and see what’s missing from the photo, the answer can also be seen on Cheltenham’s town emblem
Stop 11:
The final stop and a gorgeous place to relax after a long walk! This is the largest spa building to be built in Cheltenham, still housing the original pump
You might need to take a stroll through Pittville Park to reach this one
Map link
Question: Look up and you’ll see three statues. To the left is Asclepius, son of the Greek God Apollo and to the right is Hippocrates, Greek Philosopher. Who is in the middle?
Look for a QR code sticker on the Pittville Park information stand nearby
That’s all the stops! we hope you enjoyed the trail and learned some interesting facts about Cheltenham – if you’ve filled in your answers correctly you should have a two-word code. Pop this in at checkout (all caps, no spaces) to receive £10 off your booking with us!