The history of Oakham goes back over a thousand years with people living here much earlier too. Oakham is a beautiful vibrant market town which somehow manages to be wonderfully quiet compared to the noisy chaos of London. It makes for a great day out or even long weekend away. Our Oakham private walking tour is the best way to see it all.
St Pancras to Peterborough (~40 min), then 25 minutes to Oakham. Your guide will meet you at Oakham Railway Station or at your hotel. Train tickets not included — book via National Rail.
A Thousand Years of History in One Small Town
Beautifully quiet, wonderfully rich — the perfect antidote to London
Oakham has been a settlement for over a thousand years — and it wears that history with great charm and very little fuss. The county town of England’s smallest county is beautifully vibrant yet wonderfully quiet, the perfect place for a great day out or a long weekend away. Your guide lives here, which means you’ll discover things that no tourist map will ever show you.
From the extraordinary Norman castle with its collection of royal horseshoes, to a medieval hospital that has been caring for the sick and poor for 630 years and is still going today — Oakham is full of remarkable stories packed into a very small and very beautiful space.
Oakham Castle Hall — hung with horseshoes gifted by visiting royalty
The beautiful old Buttercross behind the Market Square — stocks intact
Hidden Gems Around Every Corner
Tom Thumb, Dead Man’s Lane & the world’s most famous signal box
As we head back through Oakham we’ll find the ancient home of the shortest man in Rutland — said to have inspired the legend of Tom Thumb. We’ll walk along a beautiful picturesque street that was once known as Dead Man’s Lane. And we’ll discover the most famous railway signal box in the world, hiding in plain sight in this most understated of English market towns.
These are the kinds of stories that only a local guide can tell — and they’re exactly what makes an Oakham walking tour unlike any other experience in the East Midlands.
Pork pies and Stilton — famous worldwide, but this is their home
Oakham’s beautiful streets — once known as Dead Man’s Lane
Just 15 minutes from Oakham by car — the enchanting Normanton Church sitting right at the water’s edge of Rutland Water, the largest artificial lake in England. One of the most magical sights in the whole of the Midlands. Ask us to include it when you book.
Pricing
Per Person — Entry Fees Included
Child prices available on request. Groups of 5–10 very welcome.
Train fare not included — book via National Rail. Optional Normanton Church add-on: +£20pp.
Book by email, via Viator, or use the booking calendar below.
Frequently Asked Questions for the Oakham Private Walking Tour
Meeting Time: AM or PM
Location: Oakham
Duration of Tour: 3-4 hours Approx
Meeting Point: Oakham Railway Station for those arriving from London (about 40 minutes to Peterborough then 25 to Oakham) or elsewhere. Otherwise we can meet you at your hotel in Oakham or mutually convenient location.
How to book Oakham Private Walking Tour
To make a booking please contact using the button above or book using the calendar system towards the bottom of the page.
Alternatively you can book by using the automated booking process with Viator by clicking below.
Don’t forget the optional extra — Normanton Church at Rutland Water is just 15 minutes away by car and utterly magical. Add it to your tour for just £20 per person. Also consider the Oakham Pub Tour for a full day in the county’s finest market town.
