Oakham and Stamford Private Walking Tour

This private walking tour explores two of the most beautiful little market towns in Britain that are only a few miles apart but which are entirely different in how they look and feel. We will spend around 3 hours in lovely Oakham before hopping 10 minutes on the train (or by car if you prefer) to Stamford. Oakham is the county town of Rutland. Our smallest county with gorgeous countryside all around and with a well-deserved reputation for its quality food and drink and artisan shops. Oakham also has a unique Great Hall in the castle, old buttercross & market & much more. Stamford is perhaps the finest Georgian-era town in Britain. You might not have been there before but you’ll likely recognise it from its many appearances onscreen. Stamford’s narrow alleyways and hidden courtyards are home to all manner of specialty shops, fine jewelers & designer boutiques. It also has a Friday Market and a buzzing High Street. Not forgetting the great history and architecture. It's heaven!

1. 1

   Oakham

   1.3 hours

   Explore charming Oakham, the county town of Rutland. We will go down all the nooks and crannies, see the bigs spots and have plenty of time if you want to bag yourself a treat. Oakham is the place if you're a foodie.

2. 2

   Oakham Castle

   20 min

   Oakham Castle gas been here since the Norman Conquest and sits upon much older fortifications. Its Great Hall is almost unique as you will see for yourself!

3. 3

   All Saints Oakham

   15 min

   You can see the Spire of All Saints Church for miles around which is handy as it gives you an idea of just how magnificent the church is inside.

4. 4

   Stop 4

   10 min

   There used to be several crosses in Oakham, now this splendid survivor is the last one and also houses the original Stocks which must have been handy being just off the Market Place.

5. 5

   Stop 5

   10 min

   The centre of old Oakham. A market is still held here several times a week and is otherwise home to a plethora of pubs, cafes, restaurants and bakeries amongst other things. Keep an eye out for the restored water pump too.

6. 6

   Stop 6

   20 min

   Oakham has a good selection of artisan craft shops, old pubs, traditional bakers, butchers and cheesemongers and even the odd swanky cafe. We will also see the home of the incredible Sir Jeffrey Hudson, a man who had a lifetime of adventures and is said to have inspired the character Little Tom Thumb.

7. 7

   Stop 7

   5 min

   It's not often Oakham makes the news, but the unveiling of the first and only memorial statue to the late Queen Elizabeth in April 2024 was that time. Come and see it for yourself. Personally I think the corgis make it!

8. 8

   Stop 8

   15 min

   Soon after we leave the station, we will pass through the gorgeous Town Meadows and cross the River Wellend.

9. 9

   Stamford's Eleanor Cross

   5 min

   A modern cross commemorating a sad moment in history.

10. 10

    Stamford Castle

    10 min

    There isn't too much left of Stamford Castle though the town walls appear here and there, sometimes where you least expect them.

11. 11

    Stop 11

    20 min

    Stamford High Street and the surrounding lanes are full of wondrous independent shops and producers. It would be rude not to check some out. I like the cheesemongers!

12. 12

    Stop 12

    10 min

    The whole of Broad Street is actually a lovely place to walk down but we will take a particular peek at this beautiful old building that is still in use today.

13. 13

    All Saints Church

    15 min

    There is no shortage of stunning old churches in Oakham and we can look at any we happen upon. If you only pick one, perhaps this should be it.

14. 14

    Barn Hill

    15 min

    Perhaps the Creme de la Creme of beautiful spots in Stamford a resident who in his own way, changed the world.

15. 15

    Stamford

    1.3 hours

    Stamford is said to be the most beautiful stone and Georgian town in England. Spend a few hours here and you'll tend to agree and you might recognise a few locations that have been used onscreen.

• Infants and small children can ride in a pram or stroller
• Service animals allowed
• Public transportation options are available nearby
• Suitable for all physical fitness levels

For a full refund, cancel at least 24 hours before the scheduled departure time.