Conquering the Cotswolds

Multi-activity event, Conquering the Cotswolds, offering morning and afternoon guided hikes for those who wish to explore the area by foot, twinned with a guided bike ride which offers two fantastic fully supported rides through the rolling hills, quiet lanes and beautiful villages of the Cotswolds – 100 miles or 100 kms.

Cycling Distance (KM)

Cycling Elevation (M)

Days Riding

Walking Distance (KM)

Walking Elevation (M)

Days Walking

This route offers plenty of flexibility and isn’t limited to the example shown here. There are many different ways to do this journey, and we can adapt it to your requirements. The options are endless, what you’ll find below is simply a typical itinerary.

Conquering the Cotswolds Itinerary

Day 1

Challengers arrive at the hotel at their leisure. Upon arrival, you will meet the pie team and bike and hike guides, who will help get your road bikes set up and go through and queries you may have. Dinner is taken at your leisure.

Day 2

The day begins with a safety briefing before heading off in your groups. The cyclists will have a choice of tackling either a 100km or a 100mile route around the Cotswolds, whereas the hikers will be transferred to the start of the hike location to take on a morning linear hike starting from the charming village of Bourton-on-Water, often referred to as “Venice of the Cotswolds”, to Kingham, 13km and 146m of elevation.

‘The team from pie certainly know how to put on a great challenge day!’ – Anna, Hertford College, Conquering the Cotswolds

The cycling routes take the cyclists through quintessentially English market towns and villages, built from honey-coloured stone. We tackle a range of rolling hills in the largest Area of Outstanding Natural Beauty in England and Wales.

The cyclists and hikers will meet up for lunch in the village of Kingham, where they can take on necessary fluids and food before setting off for the second half of their respective challenges.

In the afternoon, the hikers have the option to do a circular hike around Kingham, which is 14km and 165m of elevation, or there is also the option to do a shorter walk in the afternoon for those preferring a more relaxed stroll.

The cyclists and hikers all meet back at the hotel to compare the day’s activities and enjoy the celebration meal.

Day 3

Breakfast is taken at your leisure, before departing for home.

Example Routes

What Our Clients Say…

      
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   48 Google reviews 
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   Sally 
 17/09/2026
 
 
 Trustindex verifies that the original source of the review is Google. Superb organisation by Team PIE
  
 
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   Sarah Bower 
 16/09/2026
 
 
 Trustindex verifies that the original source of the review is Google. Four day trip from Ljubljana to Trieste. Lovely friendly staff with excellent efficient organisation. Very nice hotels  and great coffee and lunch stops - only wish they could have organised the weather too! Incredible support in tough conditions. Top notch all round.
  
 
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   Jason Bacon 
 16/09/2026
 
 
 Trustindex verifies that the original source of the review is Google. My 9th PIE organised cycle challenge for the 40tude charity. Another spectacularly organised PIE ride. The way the team and guides handled and responded to all the surprises and challenges thrown their way, making everything smooth for us punters was extraordinary. And very much appreciated. The most professional and friendly group of tour managers, support team and cycle guides. Well done to the whole PIE team and Paul & Tina. You are simply the best.
  
 
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   Greg Martin 
 16/09/2026
 
 
 Trustindex verifies that the original source of the review is Google. Event team did a great job coping with air traffic meltdown in the UK, storms in Slovenia and road closures from visiting diplomats.

accommodating, feeding and moving over 30 people on a daily basis is no easy task and they do it very well! Kudos to Paul and team.
  
 
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   James Purves 
 16/09/2026
 
 
 Trustindex verifies that the original source of the review is Google. This is probably my 6th rode with pie. They always have things organised and when something isn’t quite right it is fixed quickly and with lots of communication. Paul and the team were brilliant in Slovenia with us all. When you are cycling and out of your comfort zone the last thing you want is to worry about the logistics and pie do that all for you. Thanks And see you soon at the next ride!
  
 
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   Richard Plaistowe 
 05/09/2026
 
 
 Trustindex verifies that the original source of the review is Google. Pie Events helped me organise the Branditos networking cycles at the International Trademark Association Annual Meeting in London, and sorted routes and guides.  Tje rides were thoroughly enjoyable and professionally guided (and 100% safe)  Riders from all over the world participated and everyone  was effusive in their praise.  A fantastic success thanks to Pie Events.
  
 
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   Daniel Osmer 
 27/07/2026
 
 
 Trustindex verifies that the original source of the review is Google. I've just completed my second 4-day group ride managed by pie. Again, it was a fantastic experience. The 3 person pie team - a trip co-ordinator, ride guide, and on-bike medic - were all top professionals as well as great fun. It was another great trip which the whole team enjoyed. I highly recommend pie.
  
 
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   Ron Rees Davies 
 27/07/2026
 
 
 Trustindex verifies that the original source of the review is Google. 
  
 
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   Michael Taylor 
 24/07/2026
 
 
 Trustindex verifies that the original source of the review is Google. PIE is outstanding and are indeed passionate about their events.

Whether Medical, Portering, Providing Food (paying attention to dietary requirements) and Drink (morning coffee, regular rehydration electrolyte tabs, soft drinks at lunch, alcoholic beverages at the end of the day - if you like that sort of thing), excellent hotels & restaurants, - all needs catered for.

Staff - highly sympathetic & empathetic - who convert a steep hill into a mere undulation. All staff  were immaculately turned out in identical uniforms.

Bike maintenance - Brilliant
Route planning - beautiful lanes, B roads, cycle paths - superb routes.

Overall - excellent management throughout, with high empathy and support for all participants (including a cat!!).
  
 
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   John Pocock 
 23/07/2026
 
 
 Trustindex verifies that the original source of the review is Google. Many many thanks for all your team’s support and guidance over the last 4 days. You provided perfect guides and excellent on the spot management. Your ride support team were always on hand to help and kept our water and salt levels up at all times. Your team were really professional and our whole group gelled around them.

Of us 8 riders who did the whole 260 mile trip, we have all gone away absolutely delighted with the achievement AND the organisation provided by yourselves.
  
 
  
  
 
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