Explore Maidstone’s Rich History on Foot


Captivating stories, history on your door step, a unique experience that combines education and entertainment. StepIntoThePast was setup to tell the history of Maidstone in a fascinating walking tour which lasts around 2 hours and covers the towns history from the start of time right up to today.

Discover Our Passion for History

Lasting around two hours, the tour is ideal for anyone with an interest in historical events and engaging storytelling.

Cost is just £15 per person – Please note, our tours are only in English

Our Guided Walking Tour Services

Historical Tour

Themed Walk

Private Group Tour

Educational Experiences

Discover Your Next Adventure Today

Book your guided tour now and step into the vivid stories from Maidstone’s remarkable past. Don’t miss out on this unique experience!

Maidstone Walk

1835 Market Town
1922 Electric Bus
Detailed view of a medieval knight's steel gauntlet grasping a sword, highlighting historical armor.
1648 Battle of Maidstone
Dark eerie skull image with a moody atmosphere from the Paris Catacombs.
1381 Peasants Revolt
From above of judicial symbols consisting of Scales of Justice and small judge hammer with curly handle
1076 Law and Order

What Our Guests Are Saying

A Hidden Gem of History in Maidstone
Over the last few years, I’ve spent a lot of time in Maidstone going about day-to-day tasks—but after joining the Stepping Back in Time walking tour with Daren, I was genuinely blown away. I never realized just how much rich and fascinating history was right under my nose. The town is filled with fabulous buildings, hidden ancient bridges, beautiful riverside walks, and tranquil green spaces that I had simply overlooked.
Daren’s tour was paced perfectly and packed with interesting stories and facts. His knowledge of Maidstone and wider historical context is clearly extensive, and he delivered it all in a way that was fun, engaging, and inclusive for everyone on the tour.
There’s even the Maidstone Museum to explore—I’ll be saving that for another day!
Whether you’re a local or visiting from afar, I can’t recommend this tour enough. I’d happily do it again and would join any other tour Daren offers. A truly eye-opening experience!

Liz

Fascinating walk. I didn’t realise there was so much history in Maidstone and how important it’s location was in terms of industry. Daren was extremely knowledgeable and had planned the walk carefully, starting at the train station, walking down to the river and along the bank to the Archbishops Palace, stopping from time to time with snippets of history. We then walked up Gabriel’s Hill to Jubilee Square where Daren explained about the markets in the town. Across to Fremlin Walk, named after a brewery which used to be there. From there across the shopping centre to where Maidstone museum is. Then finishing the walk outside the prison. It was 2 hours well spent and Daren made history interesting!

Doreen

I wasn’t sure what the tour would be like, or how much Maidstone had to offer historically. We were pleasantly surprised and the 2 hours flew past! Darren brought to life Maidstone’s rich history with a blend of facts, stories and quirky details. It was a fantastic thing to do on our doorstep and I look forward to sharing this experience with visiting friends

Claire and Toby

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Ready to Uncover History?

Join us on a historical adventure today. Step into the past and experience Maidstone like never before!

History Hit

It’s long been rumoured that Maidstone Prison was built on the bones of executed prisoners. The story traces back to 1818, when sand for the prison’s foundations was quarried from nearby Penenden Heath. The name Penenden is believed to derive from the Old Saxon word penia, meaning “punishment,” and for more than a thousand years the heath served as one of Kent’s principal execution grounds.

Those who were hanged were often buried where they died, and over centuries the ground absorbed countless unmarked graves. It’s therefore entirely possible that human remains were mixed into the sand later used to build the prison’s foundations—giving unsettling weight to the legend.

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