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Oakham Castle

Oakham & Uppingham

Self-guided walks for the Curious...

Explore Oakham & Uppingham town centres with two self-guided heritage walks with a treasure hunt theme. Discover Oakham & Uppingham's "hidden treasures" whilst having a fun day out with family and friends!
Oakham and Uppingham are charming market towns in Rutland, England's smallest county at 151 square miles. Rutland is the only county not to have a McDonald's (or Burger King or KFC!), and not to have any static speed cameras, but it does contain the UK's largest man-made lake. Its residents are known as Raddlemen. Oakham hosts the World Leg Wrestling Championships each year, and Stephen Fry attended Uppingham School, until he was expelled at the age of 15!


Code Curious20 at checkout for 20% discount on purchases over £12

The Booklet

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Curious About... Oakham & Uppingham

  • An exploration of Oakham & Uppingham's town centres with two self-guided heritage walks with an optional treasure hunt. Completing the treasure hunt keeps everyone actively engaged, and urges you to look up, down and every which-way - so you won't miss out on any of the towns' treasures.
    Explore, Discover, and Enjoy!
  • Most clues are chosen for their historical value, so you'll learn about the diverse culture, significant people and extraordinary events which have influenced Oakham & Uppingham in becoming what they are today.
  • This is an outdoor, unsupervised activity - so you can go at a pace which suits you, whilst keeping you healthy!
  • A Curious About walk is a fun and social activity for all the family and friends. Different people can take on different roles - follow the map, identify picture clues, read directions, etc - it's ideal for children from the age of 6, and if you can walk/wheelchair it, you're young enough!
  • The two walks are in different, though nearby, towns. Do both, or have a breather and do the second one another day! They both start and finish in the heart of the town - so buses, trains and car parks are easily available to get you there and back.

1. Oakham - 1.5 miles / 2.4 kms
On this route you’ll see most of Oakham’s notable tourist attractions: a picturesque park; the 12th century hall of the Norman castle, with a unique collection of aristocratic horseshoes; the County Museum which tells the story of Rutland, and the house where Britain’s smallest man lived. But not only that, you’ll pass by some fascinating and quirky shops, and finish at the market place with its ancient octagonal Butter Cross and stocks!
Cutts Close Park The Butter Cross, Market Place   1.5 hoursNot OK for wheelchair users

2. Uppingham - 1 mile / 1.6 kms
Take a walk around this pretty market town in Rutland, starting at Uppingham School with its impressive buildings and history dating back to the 16th century. Now head back into the town centre with its appealing market square and quaint shops, tea rooms, pubs and restaurants before looping back to the 15th century parish church, to finish at the Square.
Uppingham School Market Place   1 hourOK but diversion maybe needed

Each booklet has a page dedicated to the history of both towns and 2 pages summarising each walk with suggestions on what to visit along the way. Walk 1 has 21 clues & walk 2 has 14 - both with detailed directions to follow. There are interesting stories about important people, places & events along the way; detailed instructions on how to find a clue if you're stuck; and a comprehensive map with the routes marked on.
Buy a booklet by clicking on the Add to Basket button, then either checkout, or continue shopping. Checkout takes you through payments via a quick & secure process managed by a third-party company called SendOwl. At the end of the payment process SendOwl will email you a confirmation email (inc download link if relevant).

You have 14 days to complete your download, and up to 3 attempts are permitted. If you buy the print-at-home version you will need to print it on normal A4 paper and the email you receive, with the download link, explains how best to fold the pages to make it into an A5 booklet. If you buy the download to mobile version you will need pdf reading software on your phone or tablet, eg using the Adobe Acrobat App (free).

Printed Copy
The booklet has a flexible cover, which has been professionally printed. The inside pages are printed to order, to ensure that they are as up-to-date as possible. We post booklets out 1st class Royal Mail, usually the same, or next working day. A small postage & packing charge is added.

"Great idea to include both towns, they really gave us an excellent feel for Rutland. We particularly liked the walk round Uppingham, somewhere with great character and charm. Thanks a lot."

Latest Revision : March 2023

Oakham & Uppingham

Places you'll pass along the way - tap an image for more detail