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United Kingdom

Oxford and the Cotswolds

Self-Guided Leisure Cycling Tour




8 days

Prices from

$2,245 P.P.


This holiday is well-suited to both regular bikes and pedal assist e-bikes, and you can choose to hire either when you book your holiday with us. Confident cyclists will enjoy the boost from a battery for those cheeky climbs, and with less effort required on the bike, you’ll have more energy at the end of the day for off-the-bike activities.  

From the charming cycling city of Oxford, this tour takes in a week of beautiful cycling through some of the most quintessentially English countryside you can imagine. This 8 day circular tour, taking in the northern Cotswolds and Shakespeare's Stratford-upon-Avon, offers everything you could want from a leisure cycling holiday - quiet lanes and cycle paths, rich history and architecture, arts and culture, charming traditional inns serving delicious meals, and green, rolling landscapes dotted with picturesque postcard villages.
The riding is gentle overall with daily distances giving plenty of time for stops at the many beautiful and historic sites you pass during each day. The northern Cotswolds offers hills aplenty, but our itinerary cherry-picks the best rides and sees the few cheeky climbs spaced out evenly throughout the week. Whether riding an e-bike or standard hybrid, you'll find the rides contain just the right balance of exertion and easy miles, keeping the focus squarely on the tremendous Cotswolds views around every corner.
In Oxford our friendly local representatives will provide a warm welcome and point you in the right direction, helping put in context the famous sights and landmarks you'll encounter over the next week.
With one enchanting view after another, the riding never gets old in this part of the world. To recharge you'll be spoilt for choice with exceptional options for lunch, refreshments and evening meals along the way, featuring delightful country inns, cafes and tearooms with some of the UK's finest local produce proudly featured.
By the time you return to Oxford after seven days of riding, having been immersed in rolling countryside, chocolate box villages and charming market towns, you'll be ready once again for a bit of hustle and bustle, with a chance to extend your stay if you wish.
For those left with an itch for even more riding, why not consider continuing on our other new self-guided tour starting nearby in Lechlade, the highest navigable point on the River Thames, and riding over five days to London taking in the Chilterns and Windsor Castle on the way?


  • Exploring Oxford the City of Dreaming Spires
  • Riverside relaxation in Bourton-on-the-Water, the “Venice of the Cotswolds”
  • Medieval market town Stratford-upon-Avon, Shakespeare’s birthplace
  • Leisurely riding through beautiful rolling countryside
  • Cycling through charming chocolate box villages
  • Stately home of Blenheim Palace with 2000 acres of gardens and magnificent architecture

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Day 1
Arrival into Oxford
Non Cycling Day

On your arrival into Oxford you’ll check into your accommodation where you will find a welcome pack waiting for you, containing information about your holiday including points of interest, places to eat and drink, and other useful local info.

Oxford offers much to see and the choice is yours. You can explore the historic University of Oxford, the oldest in the English-speaking world, and see its many iconic buildings spread throughout the city centre. You might wish to take in the view from atop St Martin’s Tower (also known as Carfax Tower), to survey the city’s iconic skyline of majestic spires.

The city is a bustling place alive with arts and culture, with numerous museums, galleries, theatres, concert halls and exhibits to choose from. Many are free of admission charges. Oxford Castle has a long and rich history and is well worth a visit. For food and drink the options are plentiful to suit all tastes and budgets, with fine dining options mixed in with fashionable and affordable student favourites.

Day 2
Oxford to Minster Lovell
24 Miles / 38 Kms Approx.
  • Meals: Breakfast
  • Ascent: 250 Metres Approx.

This morning you’ll be met by our local representative who will provide you with your hire bikes, if hiring, as well as an explanation of the days ahead with helpful tips on points of interest along the way. A gentle ride introduces us to the region with only a small amount of climbing today.

Heading north out of Oxford we‘re quickly out of the city and riding along the River Thames toward the ruins of Godstow Abbey. You’ll progress along gentle countryside lanes, through the villages of Wolvercote, Yarnton and Hanborough with a great selection of traditional pubs and cafes along the way as well as numerous galleries and museums (Oxford Bus Museum & Morris Motors Exhibition in Hanborough is worth a stop if open on the day you pass through). After passing Eynsham Hall Park (well worth a diversion) and through North Leigh, Hailey and Crawley you’ll soon finish in the pretty village of Minster Lovell on River Windrush, not far from the market town of Witney.

With three parts, Old Minster, Little Minster and New Minster, there are various sites to explore including the ruins of Minster Lovell Hall, as well as a few traditional inns and a gastropub. Plenty of green and tranquil spots to relax can be found here at the edge of the Cotswolds, providing a nice contrast from the bustle of Oxford.

Day 3
Minster Lovell to Bourton-on-the-Water
19 Miles / 31 Kms Approx.
  • Meals: Breakfast
  • Ascent: 350 Metres Approx.

Today you’ll enter the Cotswolds Natural Landscapes and ride through some picturesque Cotswolds villages with architecture dating back to the 11th century. You will encounter some of the first beautiful Cotswolds views of the holiday which invariably means some hills are involved. Rest assured though that today’s ride is still relatively short with little climbing overall.

Numerous pretty villages along today’s route host excellent pubs, cafes and tearooms, whether you stop in Swinbrook, Burford, Barrington or Sherborne. The first half of the ride follows the River Windrush until reaching the village of the same name. Approaching Farmington you’ll encounter a climb, before reaching the Golden Jubilee Tree at its summit.

Heading north you climb to the day’s highest point (still only about 200m high), before a fun descent into Bourton-on-the-Water. With plenty of time to explore, take the opportunity to visit Bourton’s many quaint shops, cafes and attractions. Some favourites include the Motoring Museum & Toy Collection, the Model Village, Birdland, or simply picking a comfy seat along the River Windrush and watching the ducks (and the world) go by. Cap off your evening with an ice cream by the river before a good night’s rest.

Day 4
Bourton-on-the-Water to Moreton-in-Marsh
31 Miles / 50 Kms Approx.
  • Meals: Breakfast
  • Ascent: 600 Metres Approx.

Today’s ride takes you deeper into the heart of the Cotswolds to experience even more outstanding natural beauty and historical wonders dating back to Saxon times. With some of the best views of the holiday, you can expect some cheeky climbs! The hilliest day of the tour still presents a very achievable challenge with plenty of time and stopping points along the way to split up the day.

If setting off a bit later, then it’s worth stopping off for a magnificent lunch at the revered Hollow Bottom Inn at Guiting Power. Soon after you’ll make your way up to Broadway Tower via Snowshill to enjoy the beautiful views before heading through Chipping Campden, famed for the most desirable high street in England and onwards to our final destination, Moreton-in-Marsh, One of the principal market towns of the northern Cotswolds dating back to the 13th century, Moreton has much to see with an abundance of shops and eateries to suit all tastes.

Day 5
Moreton-in-Marsh to Stratford-upon-Avon
24 Miles / 39 Kms Approx.
  • Meals: Breakfast
  • Ascent: 200 Metres Approx.

From Moreton-in-Marsh we ride on into a more rural side of the Cotswolds, where you can witness the agricultural side of daily Cotswold life. Expect to visit a number of very pretty and quiet villages and enjoy fantastic views across the famed rolling hills.

You will briefly leave behind the Cotswolds whilst exploring Warwickshire and finishing at the birthplace of William Shakespeare in the historic market town of Stratford-upon-Avon. It’s a leisurely ride today, whether you cycle steadily to enjoy a bit more time in Stratford, or choose to go at a very relaxed pace to take in the rural life and scenic villages and towns like Shipston-on-Stour and Ilmington (which comes at the end of the day’s only sustained climb).

For those wanting to take in the theatre in Stratford we strongly recommend pre-booking. In addition to the town’s many theatres there are many historic sights and buildings, guided tours, exhibits and attractions as well as plenty of shopping opportunities. We recommend Anne Hathaway’s Cottage, where Shakespeare’s wife was born and raised – a beautifully preserved old english farmhouse complete with a lovely cottage garden and orchards.

Day 6
Stratford-upon-Avon to Kingham
33 Miles / 53 Kms Approx.
  • Meals: Breakfast
  • Ascent: 550 Metres Approx.

Today is the longest cycling day of the holiday and probably one of the most challenging, comparable in distance and climbing to Day 4 riding to Moreton-in-Marsh. From Stratford you will venture back into the heart of the Cotswolds. The riding today offers fantastic views of the unspoilt rolling hills and more chances to visit small picturesque villages, historic settlements and the famed town of Chipping Norton.

Thankfully the first half of the ride is relatively flat and undulating, rising subtly until just before the villages of Cherington and Stourton where you re-enter the Cotswolds. Your legs will know you‘re back in the Cotswolds, as you rise further to Whichford and then a cheeky climb straight after.

Passing Little Rollright and the Rollright Stones, you have a chance to explore these neolithic and bronze age boulder monuments before a downhill section and one last climb and descent to the village of Kingham for your overnight stay.

Day 7
Kingham to Woodstock
27 Miles / 47 Kms Approx.
  • Meals: Breakfast
  • Ascent: 450 Metres Approx.

Today’s ride is shorter with less climbing overall, but does contain a few cheeky climbs, which thankfully are mostly in the first half of the ride. From Kingham you spend the morning riding through the last of the Cotswolds villages you’ll see on this tour, with a few good options to stop for lunch before the terrain flattens out.

Riding on toward Woodstock you take in more pretty countryside and arrive at your destination via an off-road path surrounded by nature. Woodstock is a historic Oxfordshire market town home to the UNESCO World Heritage Site of Blenheim Palace, the seat of the Duke of Marlborough and one of England’s largest houses. The palace is notable for many reasons, including being the birthplace of Winston Churchill. Those interested in history, fine art, and English history will all find plenty to enjoy and hours can be spent enjoying Capability Brown’s stunningly landscaped park – the quintessential landscape of the English aristocracy. The palace, park and gardens are open to the public for an entry fee.

Day 8
Woodstock to Oxford
17 Miles / 27 Kms Approx.
  • Meals: Breakfast
  • Ascent: 100 Metres Approx.

Today is a very easy day providing a chance to enjoy the tranquillity of the canal waterways and to explore a different side of Oxford city.

The aim is to arrive back into Oxford at lunch time, where after lunch there is the opportunity to explore the castle, see more of the dreaming spires and explore any of Oxford’s colleges and attractions you haven’t yet had a chance to see.

After riding through the old part of the city, you’ll finish your tour under Oxford’s own “Bridge of Sighs” (a skyway used by students commuting between lessons over New College Lane, bringing to mind the better known Bridge of Sighs in Venice). It serves as a memorable finish point to your holiday, adding to the many iconic sights you’ve taken in over the last week.

Your local representative will meet you with your luggage, collect hire bikes as needed and wish you a pleasant onward journey or extended stay in Oxford.

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The Cycling


The Cotswolds is renowned for an extensive network of rolling country lanes and whilst we do occasionally have to cross slightly busier roads, the only times we really venture off the quiet lanes are when we visit some of the region’s lovely small towns and villages or when our route takes us onto occasional designated cycle paths.

The rural lanes are often very narrow but are, when away from the towns and villages, generally low on traffic, making for a peaceful and relaxed riding experience. There are sections of shared use canal towpath which are unpaved and can be narrow at times. It may be necessary to dismount and walk certain sections to pass other cyclists, pedestrians and dog-walkers.

Whilst the roads can be described as “mainly rolling” our routes do take in occasional steeper climbs but these are few and far between and are never particularly lengthy.

Although the route is relatively easy going, opting for an e-bike would make it even more relaxed and allow for more time spent exploring the sights along the way.

For more information about riding an electric bike on our holidays please click here

Oxford and the Cotswolds uses a part of the National Cycle Network, a route from the charity, Sustrans, who are working to make it easier for everyone to cycle in the UK. Skedaddle will donate to Sustrans for every mile that you and others ride on this route with us. If you fancy donating more to Sustrans, you can choose to make your own donation for the development of the National Cycle Network when you make a booking with us.

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Leisure Cycling Grade

Grade 2-3: Gentle/ Moderate

Aspects of both our grade 2 and 3 trips

Suitable for those looking for some cycle friendly routes

Some modest climbs

Possibly sections of varying terrain (eg. forest tracks, gravel paths etc)

Our grading guidelines have been carefully created based on our many years of cycling experience, as well as customer feedback from our trips. Of course, if you're still struggling to figure out where you fit on the scale, do feel free to give us a quick call and we'll be more than happy to help!

For more information about our grading system click here.

Is this suitable for you?

Trips that are graded as a 2-3, will have aspects of both our grade 2 and 3 rides. These tours are still suitable for those perhaps who have recently got into cycling, and offer an array of accessible, cycle friendly routes, cycle paths and quiet roads, however there will be some days / sections where you may have to tackle some ups and downs, the occasional steeper climb and perhaps some varying terrain (forest tracks, gravel paths etc). Suitable for those with a decent level of physical fitness, looking for some leisurely rides with occasional (achievable!) challenges along the way.  

For more information about the grading of this holiday in particular, please check out the terrain section which will give you some specifics of what to expect on this tour.

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Dates & Prices

Daily departures available from April to mid October.

For a group of 4 or more we can offer the reduced rate of $2025.

You can either make a booking online or over the phone. Once we have your details, we’ll be able to check availability.

Secure Your Holiday With A Deposit

Book now with a $250 deposit and nothing more to pay until 60 days before departure. Choose a date to start your booking and see all prices, including bike hire and single room supplements.

Select a date to view prices and book
Start Date
End Date
Price p.p.
Start Date
Return Date
8 days

Whats Included Tick

A) Accommodation (shared twin rooms)

B) Meals as per the itinerary (B=Breakfast, L=Lunch, D=Dinner)

C) Access to an app for holiday information and navigation

D) A printed map

E) Luggage transfer service

F) Local Skedaddle representative

G) Emergency tool kit, pump etc. (if renting your bike from Skedaddle)

H) Financial Protection through ABTOT

What's not Included Cross

A) Bike and helmet rental (available if required)

B) Travel or flight costs or charges for travelling with your bike (if applicable)

C) Meals not stated in the itinerary

D) Single room (available if required)

E) Travel insurance

F) Personal clothing and equipment

G) Personal expenditure (souvenirs, bar bills, hotel facilities etc)

H) Entrance fees to cultural or historical sites and visitor centres

I) Other optional activities

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The Essentials

Travel Options

The start and finish point for this holiday is Oxford. The nearest airports are London Heathrow (LHR) and Birmingham (BHX), both have direct and one stop flights connecting North America through multiple carriers. The best way to arrive to Oxford is by train, with the station well-connected to London and various other UK cities. If bringing your own bikes, you’ll need to reserve them for your train journey.

Standard accommodation options are a short walk from the station, but if you require assistance, please let us know. If you choose to drive, you will be able to leave your car for the duration of the trip at an Oxford City Council Park & Ride site for the week at a cost of approximately £30. We can advise on how best to pre-book, and about transfers from the park & ride site to your accommodation at the start of the trip, and back to your car at the finish should you need them.

At the end of the holiday, you’ll be met in Oxford with your luggage, and your bike will be collected if hiring. You’ll then be free to make your own way or be transferred back to your car if needed. We recommend that you do not book trains earlier than 12:00 on the departure day, and make sure to give yourself time to explore the city if you wish!


In the UK we use good quality 3 or 4 star hotels, B&Bs, inns and family-run guesthouses that are cycle friendly, located close to the cycling route and showcase the style and hospitality of the area you are visiting.

Where possible we prioritise locally owned businesses and those offering locally sourced food, drink and speciality products. This all promotes sustainability in-line with our responsible travel policy.

All our UK trips are operated on a double/twin-share basis. Single occupancy rooms can be provided for a supplement and are subject to availability at the time of booking.

Bike Hire

If you would like to rent a bike we have both hybrid and electric bikes available.

The hybrid bikes are generally Scott Sub Sport 30 bikes with a gear range suitable for the route and terrain, semi-slick tyres, hydraulic disc brakes and a relaxed riding position. Provided with a low step through frame for ladies and a slightly sloping top tube for gents.

The electric bikes are generally Gazelle Ultimate T10 and Gazelle Chamonix T10 pedal assist bikes with batteries suitable for the daily distances on this holiday and hydraulic disc brakes. E-bikes come with step through frames as standard.

All bikes are equipped with a rear rack, mudguards, lights, cycling computers, map holders, pannier bags, D locks and a rack pack containing basic tools including a pump and puncture repair kit.

We are also able to provide helmets, if you’d like one to be provided, please request this at the time of booking.

You are welcome to bring along your own saddles, or own pedals if renting a hybrid bike, but please let us know if advance if you plan to do so. If you are planning to bring your own e-bike, please let us know the make and model of your bike and we can check its suitability.

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News, Reviews & Stories

Your Quick Kit Guide From Endura and Skedaddle

E-bikes - everything you need to know

There’s no doubt that e-bikes are popular. We caught up with our expert to answer some of your burning questions!


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