South of England

Cotswold Cycle – 4 Nights

April, May, June, July, Aug, Sept, Oct£599 pp

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Dates may vary in price due to demand throughout the season and are subject to changes from time to time. We recommend booking your trip well in advance to secure the best pricing available for your preferred dates.

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Cotswold Cycle – 4 Nights

No. of People: 1



TOTAL £999

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Starting in the popular market town of Stroud, this classic Cotswolds cycling loop takes you on a journey through charming English countryside and pretty honey coloured villages.  Ride along quiet country lanes, past open farmland and enjoy the Cotswold Area of Outstanding National Beauty for much of its course.  You will pass stately homes, ancient battle sites and beautiful churches, all whilst being treated to some of the most amazing views in England.

Quick Facts

  • 4 nights’ accommodation
  • 4 days’ cycling
  • Guidebook and GPX files provided
  • Daily door to door luggage transfers
  • 134 total miles (215km) and 2,165m (7,105ft) of ascent
  • Ride through and explore quintessential English countryside

About & Details

Ride this fantastic loop around The Cotswolds, starting and ending in the pretty market town of Stroud. As you explore this beautiful part of the world, pass through the lovely towns of Cirencester, Winchcombe, Stow and Chipping Campden. It is a popular route, riding through green landscapes, rolling farmland, peaceful woodlands and attractive villages.

This route is perfect for anyone seeking out a taste of quintessential English countryside. Home to ancient castles, Neolithic burial grounds, idyllic villages and breathtaking views, this route offers it all. As the path meanders through the Cotswold Area of Outstanding Natural Beauty, you are treated to ever-changing views which are steeped in history and are therefore sure to make your trip a pleasure from start to finish.

We take the stress out of your trip with expert local knowledge, hand-picked accommodation, luggage transfers and detailed support to help you find your way. You can bring your own bike, or we can organise bike hire for you.

The price for this trip is based on 2 people sharing.


  • 4 nights’ accommodation in a good quality B&B or hotel with ensuite or private bathroom and breakfast
  • Luggage transfers each cycling day
  • Guide book and GPX files
  • Expert local knowledge and 24 hour emergency assistance during your trip
  • Professional event organisation
  • Travel to the start and finish points of the trip
  • Lunches and evening meals
  • Personal insurance (for cancellation, accident, health, emergency evacuation and loss, theft of or damage to baggage and personal effects)

Optional Extras

  • Single room supplement £90 per person per night (subject to availability)
  • Solo traveler supplement £90 per person per night
  • Odd group supplement £90 per group per night may apply
  • Extra bag £12.50 per person per day
  • Extra night prior to start (single room) £180 per person
  • Extra night prior to the start (twin room, needs 2 people) £95 per person
  • Extra night at the end of the event (single room) £180 per person
  • Extra night at the end of the event (twin room, needs 2 people) £95 per person

Please select from Optional Extras at checkout.

Getting there and back

Getting There

By Air: The nearest airports are Bristol, Birmingham and London Heathrow.

By Rail / Bus: The nearest railway station to Stroud is Gloucester, around 20 minutes away by car or by bus. These have regular services from London, Birmingham and Bristol. There are then various bus services to/from Stroud, or you can cycle the 10 mile route.

By Road: Travelling by car is the easiest way to get to Stroud. There are multiple car parks to leave your car for the duration of the trip.

Getting Away

By Air: From Stroud, taking a taxi will take 55 minutes to get to Bristol airport. Alternatively you can catch a train from Gloucester to reach Birmingham Airport or London Heathrow Airport.

By Rail / Bus: From Stroud, Gloucester is a 20 minute bus ride away, where you will find rail connections to Bristol, Birmingham and London.

By Road: The nearest motorway to Stroud is the M5, with connections to all parts of the UK.

Evening meals and lunches

You can purchase evening meals either at the accommodation or nearby. When our event planners send your itinerary you could prearrange directly with the accommodation or during the walk.

For lunches we would suggest bringing some of your own favourite snack bars and then asking the accommodation for a packed lunch for the following day and also supplementing refreshments en-route.


Accommodation is generally at B&B, guest houses and small hotels. Once booked in, your event planner will send you a list of your booked accommodation. It is possible to adjust according to preference at this stage so please mention it if you wish to change.

After you book

After placing your booking with us, you will in the first instance receive an automated email from our system confirming receipt of your reservation. If you don’t receive it, it is worth checking your spam/clutter folder.

In the process of placing your booking, you will generally set up an access password to our online gateway where you can review the details of the booking.

Your personal event planner will then be in touch with you to start to confirm the details. This contact will usually be taken up in the working day after receipt of your booking, but may, in busy times, take a little longer. The event planner will then liaise with you regarding the details of the course. If you have any specific requirements, please do mention it at this stage.

At the end of your trip

Unfortunately, all good things come to an end at some point and when you arrive at the end of your ride, you have one of several options. If you have not booked an additional night’s stay then we can transfer your luggage to a location of your choice. From there you may have onward travel arranged as per the ‘Getting There and Back’ tab above.

Some people like to treat themselves to a night’s stay at the end. And why not? You’ve earned it. You can arrange this as an optional add on with your event planner.

Dates and prices

For available dates please click on the ‘book now’ option on the left hand side on desktops or at the bottom on mobiles. You can reserve your space via this route.

Book your adventure


  • Day 1 - Arrival in Stroud

    Check into your accommodation in Stroud

  • Day 2 - Stroud to Winchcombe

    Your ride through The Cotswolds begins by leaving the historic market town of Stroud.  The route climbs slowly towards Longridge, with lovely views of Painswick, and Painswick valley on your left hand side. Continue cycling over undulating terrain through the quaint Cotswold villages of Withington and Charlton Abbots, before reaching the market town of Winchcombe and your accommodation for the night.

    30 miles (48km) and 769m (2525ft) of ascent.

  • Day 3 - Winchcombe to Stow-on-the-Wold

    The route today begins with a steep, meandering climb out of Winchcombe, passing Sudeley Castle on route. Reaching the top of Sudeley Hill, you are rewarded with magnificent views.  Continue into the village of Snowshill, which in the summer is surrounded by colourful lavender fields that turn a wonderful shade of purple. Chipping Campden is well known as a centre for the Arts and Crafts movement; be sure to explore this historic town, with many of the old buildings still used as craft workshops today.  Enjoy your night in Stow-on-the-Wold.

    30 miles (48km) and 655m (2150ft) of ascent.

  • Day 4 - Stow-on-the-Wold to Cirencester

    Despite being the longest day of the trip, the riding is much easier-going today, traversing rolling countryside over smaller, and less steep sided hills. Following the route, ride through Bourton-on-the-Water, which is knows as the ‘Venice of the Cotswolds’, with many pretty bridges crossing the River Windrush. Continue cycling through the rolling Cotswold hills, and historic villages such as Great Barrington, which has been an agricultural settlement since Roman times. Reach the bustling town of Cirencester and enjoy exploring the many local boutique shops and cosy pubs.

    40 miles (64km) and 434m (1325ft) of ascent.

  • Day 5 - Cirencester to Stroud

    Follow gentle cycle paths out of Cirencester, and around the edges of Cirencester park, which is part of the Earl of Bathurst’s Estate. Continuing on through Sapperton and Cherington, reach the lovely Cotswold town of Tetbury. Enjoy wonderful lasting views of the Cotswolds as you ride along this final section of the route before reaching Stroud, where you can celebrate the end of your journey.

    34 miles (55km) and 450m (1475ft) of ascent.


Please note: This itinerary is a guide only. It can be subject to change dependent upon viability, course members’ fitness, weather conditions, accommodation availability, or for any other reason that may be deemed necessary. Any timings and mileages are approximate and for guidance purpose only.

We will always endeavour to accommodate you in the locations detailed in the above itinerary. Due to very high demand, some accommodation providers may occasionally have limited availability and so we may need to accommodate you in an alternative location, nearby. In this case, we will arrange a taxi transfer for you to take you from the trail to your accommodation and back again the following morning. An additional charge may be payable. We will notify you of this when confirming your booking.

The Route

Find some of the reviews our wonderful customers have left for us below, or read them all here!

Heather Parr
3 months ago

Maximum Adventure exceeded expectations, planning a trip for me last minute and off season through the glorious Lake District. The hotels were top rate, as was the food and my daily gluten free sandwich. Nathalie got the route guide sent to me in a couple of days and the baggage service was impeccable. It was the only tour guide company that responded immediately to my last minute request. Looking forward to more adventures with your company!!!

Chris Evans
3 months ago

David and I walked the Speyside Way in September 2023 and very much enjoyed the adventure. Maximum Adventure Ltd organised our nightly accommodation and uplifting of our luggage in a seamless manner, which made the whole trip so easy with no stress. This is the second time that I have personally used Maximum Adventures Ltd and I would recommend them to others as they offer a friendly and efficient service.

Göte Fredriksson
4 months ago

We realy appreciated the tour we did on Hadrians Wall path in May.Beautiful scenery, decent weather, god arrangements including lodging, transport, bagagehandling etc. We came well prepared . In this preparation Maximum adventures gave us great support, as we are coming from abroad with no knowledge of conditions on the path. We had great BnBs and could concentrate on de daily walks that gave us great pleasure.Thank you England and Hadrians Wall path for your friendly reception and well mantained walking path.Thank you Maximum Adventures for your good service.We would love to come back in the future.

Jerry Kashinski
4 months ago

Maximum Adventure did a great job for us. With less than a month's notice, it set up an itinerary, lodging and luggage porterage for a walk from Carlisle to Newcastle, England along Hadrian's Wall. The lodging was fantastic, as was the itinerary and support during the walk. We'd definitely use Maximum Adventure again and would recommend them without reservation!

Fiona Reilly
5 months ago

I was part of a climb on 23/09, didn't think I would make ut, but I did. The descent was a different story.. I got jelly legs and lost my confidence. If it wasn't for James, my Sherpa would never have made it. Can't thank him enough, Will, met you briefly.Both of them were very knowledgeable, we had the most amazing views at the summit...the pain is still worth it and

Tom Graham
5 months ago

I walked the West Highland Way with my dad and brother. The organisation was excellent by Samantha. Itinerary and instructions were clear and all the bookings and luggage transfers went smoothly. As a result we were able to ensure the fantastic walk and not worry about anything. I would happily recommend Maximum Adventure to others.

Sarah Bracken
5 months ago

Absolutely brilliant guide - knowledgeable, interesting and humorous in addition to looking after our safety so well - making sure we ate and suggesting when to layer up! Would highly recommend!

Diana Straub
6 months ago

We just got home from our 8-days Hadrian's Wall hike and we just loved it!Everything was perfectly organized!We had great B&Bs and hotels with very friendly, welcoming and helpful staff. Our favorite was the Dacre House with Clare. But then again, all were great!The luggage was always at the day's destination, no matter how early we got to the accommodation.The description of how to get to the accommodations were clear and precise.The road map and the guide book were waiting for us as we got to the first B&B and were very helpful and interestingThanks, Maximum Adventure!

Kristin Hentschel
6 months ago

Praise for the West Highland Hike and the Maximum Adventure planners, esp. our planner Samantha. Great experience in every regard.

Simon Bradish
6 months ago

Booked for the 3 UK Peaks adventure, it was organised perfectly and everything when to plan. Accommodation was good, transport excellent, our guide (Patrick) brilliant, so cannot fault the trip and adventure. I personally expected too much from myself and was unable to fully summit as this adventure is not for beginners, I climbed Kilimanjaro in 2003 when I was 42 and twenty years later, although relatively fit, my endurance didn't last. So I did a half summit for Ben Nevis & Scafell, thanks to Patrick for letting go back down on my own, it was brilliant. With Snowdon, a half summit is tricky as you can't descend the way you go up, so I decided to do some hiking in the area while the rest of the group did the climb. I took a chance and went to the ticket office and managed to get a single return ticket up to the summit of Snowdon at 9am which returned down by 11.30am. I was hoping to see my group on top and spring a surprise but the weather was terrible. I highly recommend the trip but make sure you are fit enough otherwise as there is an emphasis on time, so a slow walk up is going to slow everyone down and really delay the trip. Have Fun, Simon Bradish

Why book with us

We know you have a choice of companies providing trips for your next adventures. Here are some of the reasons you should choose to travel with Maximum Adventure:

  • We are an established adventure travel business
  • We have been trading since 2002
  • We are financially protected in accordance with the 1992 travel regulation
  • Knowledgeable and available office staff
  • Qualified leaders and guides with ascents ranging from Ben Nevis to Mount Everest
  • All activities are risk assessed
  • We will provide you with the best service available
  • We are aware this is your holiday/your challenge and will do our best to make it an enjoyable and rewarding experience
  • We have many repeat clients stretching back over a number of years
20+ years adventure organisation experience
Full liability & financial protection
Leading provider of high quality adventure challenges
Great team of staff to support you

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