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United Kingdom

Cotswolds to London

Self-Guided Leisure Cycling Holiday




6 days

Prices from

£1,335 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.

This place to place journey takes in over 130 miles of picturesque English countryside, vibrant market towns and world famous historic sites. From the edge of the Cotswolds all the way to the capital city of London, you'll enjoy five varied and relaxing days of cycling, riding from the highest navigable point on the River Thames and winding your way, largely on riverside paths, green cycleways and quiet country lanes, finishing at Putney Bridge in the southwest of London, fittingly back at the Thames. 
Early on you'll see majestic Uffington White Horse, a prehistoric hill figure formed by deep trenches of white chalk, and cycle the nearby Ridgeway, an ancient track known as Britain's oldest road. More highlights follow as you enter the Chiltern Hills Natural Landscapes with lovely cycling lanes and chances to visit the Didcot Railway Centre, Wallingford Castle, and the 14th century Greys Court Estate.
As you leave the Chilterns you arrive in historic Henley-upon-Thames, a beautiful market town world famous for rowing and home to the famous Henley Royal Regatta. It provides yet another chance to cap a day of cycling with a cold drink at the river's edge, watching the sun set on punters along the Thames (or having a go yourselves).
From Henley you re-enter the Chilterns countryside riding mostly along secluded cycle paths and waterways, and visit some beautiful towns on your way to Eton and Windsor, with a chance to visit Windsor Castle as well as the "Long Walk" and famous deer park.
The final ride takes you into London along the Thames, passing Runnymede where the Magna Carta was signed. Hampton Court Palace follows, the favoured residence of Henry VIII and his many wives. Well worth the stop and home to the Hampton Court Maze, if you've had too easy a time navigating thus far and want to "get lost" for a while.
Approaching London you'll ride through the heart of Richmond Park, one of London's eight Royal Parks, before meeting the Thames one last time and finishing your ride at Putney Bridge.
This self-guided trip is for a minimum of 2 people and accommodation, luggage transfers and emergency back up are all included. Plentiful information on points of interest along the route, recommendations on places to eat, and more local info is provided, allowing you to relax and enjoy the ride, choosing where to spend more of your time exploring. Nothing could be simpler!
Routes have been carefully designed to allow plenty of time for a casual ride whether on hybrid bikes or e-bikes. This route, packed with history, visitor attractions and beautiful scenery is one best enjoyed slowly, making it a perfect choice for cyclists of all levels of experience.

Holiday Highlights

  • Tracing the River Thames from near its source all the way to London
  • Didcot and its impressive railway heritage
  • The impressive Uffington White Horse & Dragon Hill
  • Beautiful wooded hills and green landscapes of the Chilterns
  • World famous Windsor Castle and Hampton Court Palace
  • Traditional pubs and award-winning English wines at the home of the Royal Regatta

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Day 1
Arrival into Lechlade-on-Thames
Non Cycling Day

On arrival you can either make your own way to your first nights’ accommodation in Lechlade-on-Thames, on the edge of the Cotswolds, or we can assist you with a transfer from Oxford. Lechlade is very close to the source of the River Thames and the highest town to which the river is navigable. The town dates back to 2500BC and is now a bustling market town boasting historic monuments, some quaint shops and a few great places to eat and drink. There are parks and nature reserves nearby, along the Thames and adjacent to the many small lakes and ponds surrounding the town. A welcome pack will be waiting for you at your accommodation prior to your meet & greet the next morning before setting off on your ride.

Day 2
Lechlade-on-Thames to Wantage
27 Miles / 44 Kms Approx.
  • Meals: Breakfast
  • Ascent: 450 Metres Approx.

From Lechlade-on-Thames you’ll head through the peaceful countryside on a ride steeped in history. Your first stop is the mediaeval barn at Great Coxwell before continuing to ride through some beautiful rural villages. Stop in the quaint village of Woolstone for a fantastic lunch if you wish, with a selection of local game and produce at the aptly named White Horse pub.

After a hearty lunch, climb the hill to view the Bronze Age Uffington White Horse Hill & visit the spot where legend has it, St. George slayed the Dragon. From here you’ll join the Ridgeway, Britain’s oldest road used since prehistoric times by travellers, herdsmen and soldiers alike. You’ll soon visit the Neolithic tombs of Wayland’s Smithy and the legendary Blowing Stone used by King Alfred whilst traveling through the villages in the ancient kingdom of Wessex. It’s mostly downhill to your accommodation, located in the historic market town of Wantage, notable for being the birthplace of King Alfred the Great in 849AD. Take your pick of the many shops, museums and monuments, cafes and pubs and celebrate your first day in the saddle.

Day 3
Wantage to Wallingford
22 Miles / 36 Kms Approx.
  • Meals: Breakfast
  • Ascent: 200 Metres Approx.

Today you’ll explore more rural villages and get to know England’s industrial railway, some haunted countryside and sample some award-winning English wine at a local vineyard. Leaving Wantage you’ll follow off-road countryside cycling routes before arriving into the busy industrial town of Didcot. Didcot is famous for the great age of steam and the railway centre is well worth a visit to learn more about the fascinating history including items from Brunel’s illustrious career.

Leaving behind the bustle of the town you’ll continue your journey riding past the picturesque Wittenham Clumps, once described by Artist Paul Nash as “a beautiful legendary country haunted by old Gods long forgotten”. The Clumps as they are affectionally known are home to England’s oldest beech trees and the site marks some of the earliest settlements in England. A good place for lunch is the charming Roman village of Dorchester-on-Thames. Dorchester is famous for its grand Abbey which is built on the site of a Saxon Cathedral. It’s a typical quaint English village boasting fantastic traditional and modern pubs, a farm shop and the tea room at the Abbey.

From here, ride on through countryside and villages until reaching an award-winning English vineyard. The vines are grown on the chalky soil and produce wines of excellent quality well worth sampling before heading into the market town of Wallingford, your overnight stop, with Wallingford Castle and plenty other sights to explore.

Day 4
Wallingford to Henley-upon-Thames
22 Miles / 36 Kms Approx.
  • Meals: Breakfast
  • Ascent: 400 Metres Approx.

Today is all about the Chiltern Hills, a National Landscape. You’ll experience the Chilterns in all her natural beauty and end the day in historic Henley-on-Thames. In the morning you’ll get the bulk of the climbing out of the way in the first few miles as you venture up into the Chilterns, an area known for its history and unspoilt landscape boasting ancient trees and an abundance of wildlife. The climbing into the hills affords you fantastic views across many counties.

Visit the Maharajah’s Well, one of the Victorians’ quirkier additions to our countryside. The Chilterns hosts a fantastic selection of pubs and cafes to choose from when you‘re feeling peckish. After coasting through a number of quintessentially English villages you’ll pass Greys Court, now a National Trust site. The country house and gardens has a rich history and has been used as a filming location for Downton Abbey, Poirot and Midsomer Murders, among others.

Before long you descend to the 12th century town of Henley-on-Thames. Henley is a world-renowned centre for rowing, each summer hosting the Henley Royal Regatta attracting rowers and visitors from across the globe. Expect good food, good views and plenty of activity at the riverside before a comfortable night’s rest.

Day 5
Henley-upon-Thames to Windsor
25 Miles / 40Kms Approx.
  • Meals: Breakfast
  • Ascent: 300 Metres Approx.

Today is once again chalk full of history, following routes that have been historically used by Kings & Queens. Riding from Henley you’ll end up in the Royal Borough of Winsdsor and have the opportunity to visit Windsor Castle, one of the British monarchy’s official residences. As you leave, navigate the picturesque Hambleden Lock over the River Thames and head back into the Chilterns for a short time.

For lunch why not stop in the lively town of Marlow, with a great selection of options. The final notable hills of the day follow, but soon enough you‘re riding at the water’s edge, along the Jubilee River, Dorney Lake and reuniting with the Thames at the end of the ride after passing through the grounds of the exclusive Eton College. You can take some time to explore this world-famous academic institution before crossing the Thames into Windsor to visit the famous castle which dominates the town. It was built in 1070 by William the Conqueror and the site consists of many historic buildings and monuments, extensive gardens, and its famous Long Walk and deer park. Windsor remains home to Britain’s royal family and can be explored on arrival before tucking into dinner at one of many fine local eateries.

Day 6
Windsor to Putney Bridge, London
36 Miles / 58 Kms Approx.
  • Meals: Breakfast
  • Ascent: 250 Metres Approx.

While your final riding day is a bit longer in length, it’s mostly flat save for some climbing soon after departing Windsor. Not to worry though as those climbs are well worth it, providing tremendous views of the Windsor monuments and Long Walk and excellent photo opportunities.

After passing through Old Windsor, you’ll pass the location where the Magna Carta was signed, as well as several other monuments and landmarks nearby. Sticking to the Thames for a while, you’ll get some easy miles in before reaching Hampton Court Palace, another recommended place to visit.

Passing by Kingston upon Thames and upon reaching Teddington Lock, you’ll leave the Thames one last time to head up and through Richmond Park, for some nature and tranquility before making your way back to the Thames across the river from Fulham Football Club’s Craven Cottage, and following the Putney Towpath for a short stretch to finish this historic ride at Putney Bridge.

Here you’ll be met by your local representative with your luggage, who will either assist with your onward journey or transfer you back to Lechlade or Oxford. Well done on completing this fantastic journey!

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The Cycling


This holiday’s riding is on a mix of cycle paths, bridleways, canal paths and quiet country roads. Overall the route is about 75% paved and 25% unpaved (but non-technical) surfaces. There are a few short sections on busier roads including some of the roads in the market towns including overnight stops.

Some canal paths include low bridges overhead and it’s advised that if you‘re in any doubt, or if advised by signage that you get off and push. Some canal and waterway paths can be busy at times with other cyclists, pedestrians, dog-walkers, and those accessing boats and barges. These sections are generally tranquil shared spaces and it’s best to ride slowly and sensibly, prepared to stop and advisable to use a courteous bell to let people know you‘re passing through.

Though the unpaved terrain is non-technical in nature, canal paths and bridleways can be bumpy or have the occasional tree branch to avoid. On any such section or a narrower stretch, if in doubt getting off and walking is advisable. There is relatively little climbing overall, though there are a few cheeky climbs, notably the climb up to the White Horse, the start of the day from Wallingford, entering the Chilterns after crossing the Thames at Mill End and a few climbs after starting out from Windsor.

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

This holiday 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 holidays

Suitable for those looking for some cycle friendly routes

Features 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?

Holidays that are graded as a 2-3, will have aspects of both our grade 2 and 3 holidays. 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 £1155.

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 £200 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
6 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) Printed route information

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

This holiday begins in Lechlade-upon-Thames on the edge of the Cotswolds and ends at Putney in London.

As a linear tour following the River Thames to London we recommend arriving by train into Oxford where we will meet you for your transfer to your first night’s accommodation in Lechlade-on-Thames. Oxford train station is well-connected to London and various other UK cities. If bringing your own bikes you’ll need to reserve them for your train journey.

The route finishes at Putney Bridge, where you’ll be met by the local rep with your luggage and hire bikes collected. They can help facilitate your onward travel with Putney train station just to the south, or Putney Bridge underground station just north of the river.

If you are driving to the start of the tour then we can advise of parking options in Lechlade-upon-Thames. We can also offer a transfer back to your car at the end of the trip for a supplement of £165 (per transfer of 2 to 4 people).


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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