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!

Meeting Point

Oakham

Oakham LE15 6QT, UK

Just outside Oakham Railway Station. Let me know your train and I will be there. Otherwise I can meet you anywhere in Oakham if you're staying in a hotel.

What's included:

• Private Tour Guide

Not included:

• Food or drink
• E/Way train tickets between Oakham+Stamford about £5. Tell me if you want me to get them.

What to expect:

Duration: 6 hours

Oakham

Oakham

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.

1 hour, 20 minutes

Oakham Castle

Market Place, , Oakham, LE15 6DT

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!

20 minutes

All Saints Oakham

Church Street, Oakham, LE15 6AA

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.

15 minutes

The Butter Cross

68 Market Pl, Oakham LE15 6DT, UK

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.

10 minutes

Oakham Market

Oakham LE15 6BQ, UK

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.

10 minutes

High Street

High St, Oakham LE15, UK

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.

20 minutes

Statue of Elizabeth II, Oakham

8 Catmos St, Oakham LE15 6HW, UK

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!

5 minutes

Town Meadows

15 Bath Row, Stamford PE9 2QU, UK

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

15 minutes

Stamford's Eleanor Cross

Sheep Market & Castle Dyke, Stamford, PE9 2QZ

A modern cross commemorating a sad moment in history.

5 minutes

Stamford Castle

Warrenne Place, Stamford, PE92NX

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

10 minutes

High Street

High St, Stamford PE9, UK

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!

20 minutes

The Hospital of William Browne: Merchant 1410-1489

3 Broad St, Stamford PE9 1PG, UK

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.

10 minutes

All Saints Church

All Saints Place, Stamford, PE9 2AG

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.

15 minutes

Barn Hill

Stamford

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

15 minutes

Stamford

Stamford

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.

1 hour, 20 minutes