Oakham Castle

Oakham &

Self-guided walks for the Curious...

Explore Oakham & Uppingham 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


Curious About Sample Booklet

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Closest Curious Walks

    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! Each starts and finishes in the heart of the town - so buses, trains (Oakham only) and car parks are easily available to get you there and back.
  • One booklet is suitable for up to 4 people, and is available to instantly download on purchase for printing at home or for using immediately on your mobile device, or we can print it for you and send it using 1st class Royal Mail.
Curious About... Oakham & Uppingham

Two walks are included in the booklet, one in either town.

1. Oakham - 1.5 miles / 2.4 kms

On this route you’ll see most of Oakham’s notable tourist attractions : the market place with ancient octagonal Buttercross and stocks; the 12th century hall of the Norman castle, with 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 a picturesque park!
The Market Place Cutts Close Park   Children's University logoChildren's University event1.5 hoursOK but small diversion maybe needed

2. Uppingham - 0.9 mile / 1.4 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.
Children's University logoChildren's University event1 hourOK but diversion maybe needed

The Booklet
Oakham & Uppingham Booklet

Each booklet is A5 size. You can: a) download to your computer & print; b) download to your phone or tablet (different format) & use directly from there; c) order a pre-printed copy which we post to you. Each has a page dedicated to the history of the city; 2 pages summarising each walk with suggestions re what to visit along the way. Walk 1 has 21 clues & walk 2 has 14 - both with detailed directions to follow. There are stories about important people, places & events along the way; detailed instructions how to find a clue if you're stuck; a comprehensive map with the routes marked on.

When you click on the Add to Basket button a pop-up asks if you want to checkout using Stripe (default) or Paypal, or continue shopping. If you decide to checkout you are taken 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).


Download files are typically between 3 and 6 mb. 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). Please see our FAQs page for further information.

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 postage & packing charge of £1.49 is made for 1 or 2 booklets within the UK. 3 to 6 booklets it's £2.25, and after that it's £4.35. Outside the UK it's £2.50 for 1 booklet, £3.80 for 2 booklets, £5.30 for 3 to 6 booklets and £10.75 after that.

Children's University Logo
If you are enrolled in the Children's University you can now gain hours towards your next award by completing one or more of our many Curious About walks.
Please note, for safety reasons a child should be accompanied by an adult, either parent/carer or person in loco parentis. Also, the booklets may require a degree of interpretation by an adult, as well as support and guidance.
To get your Children's University sticker:
  • Buy the download or booklet (which will contain two walks).
  • Complete one or both walks in your own time.
  • Complete the Returns Form below and send it to us:
    Complete one form for each location (eg Oakham & Uppingham).
    Let us know one additional interesting fact you discovered along the route for each walk you complete (this provides proof that you did it / them).
  • We will then send you an email with your sticker, which you can print, cut out and stick in your passport. Hours awarded will equal those shown against each walk.
What People are Saying!

"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 : May 2019