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New Route

Historic England: Castles and Palaces

Explore Oxford, the Thames Valley and the Chiltern Hills

Flag great britain Great Britain

  • Region Region South-East England
  • Tour Type Tour Type Guided (Scheduled Departure)
  • Duration Duration 6 days
  • Bike Type Bike Types Hybrid, Touring & e-bike

Core Route

150 Miles
2 (Moderate) Difficulty Level: 2 (Moderate)
Average Distance per Day: 30 mi
0 100 mi
Average Elevation Gain per Day: 243 yds
0 500 yds

Extended Route

150 Miles
2 (Moderate) Difficulty Level: 2 (Moderate)
Average Distance per Day: 30 mi
0 150 mi
Average Elevation Gain per Day: 243 yds
0 500 yds
May - September from
Next Steps


This is a beautiful, guided, all inclusive and relaxing tour through the historic University city of Oxford and the surrounding area. Oxford, The City of Dreaming Spires, is famous the world over for its University and place in history. For over 800 years, it has been a home to royalty and scholars, and since the 9th century an established town, although people are known to have lived in the area for thousands of years. Nowadays, the city is a bustling cosmopolitan town, with a mixture of ancient and modern.

The countryside surrounding the city is quintessential England in all it's glory, littered with rolling green hills, quaint villages, spectacular castles and palaces, and magnificent, quiet country lanes and river towpaths that make it an ideal cycling destination.

We will see the University, punting on the River, Windsor Castle, Blenheim Palace and plenty more...

This tour runs from Monday to Saturday on the following dates:

Monday 6th May

Monday 3rd June

Monday 24th June

Monday 8th July

Monday 22nd July

Monday 5th August

Monday 26th August

Monday 9th September


  • Oxford University

  • Blenheim Palace

  • Windsor Castle

  • Eton School

  • Punting on the River Thames

  • The Chiltern Hills

  • Waddesdon Manor

  • Hellfire Caves

What's included

  • 5 nights hotel accommodation with breakfast

  • Local Cycling Guide for 6 days cycling

  • Hybrid Bike Rental

  • Luggage Transfers

  • Entry to Blenheim Palace, Windsor Castle and Waddisdon Manor

  • Oxford Walking Tour

  • Tickets for Punting on the river

  • Entrace to the Hellfire Caves

  • 5 lunches

  • Pre-trip planner

  • All routing, maps, cue sheets and gpx tracks

  • Regional Handbook

What's not included

  • Upgraded Bike rental
    Road, Gravel and E-Bikes available to rent

  • Evening meals

Optional Costs

  • Gravel bicycle rental

  • Road bicycle rental

  • Electric bicycle rental

Day 1

We meet on our first night at our hotel in central Oxford were we will have a meet and greet and ride briefing before dinner.

Day 2

Itinerary: Oxford Loop via Blenheim Palace (23.2 miles)

Head through Oxford on small back streets from the hotel for three quarters of a mile until picking up the canal towpath. Ride approximately 4 miles along the canal towpath, enjoying the solitude of a traffic-free route out of the city.

Today’s highlight is a visit to Blenheim Palace. This spectacular stately home was the birthplace of Sir Winston Churchill. You will have approximately 3 hours available to you to tour the house, gardens and magnificent parklands. The guide will provide a picnic lunch in the designated picnic area with tables and benches, which will be available any time between 12:00 and 13:00. We then have the opportunity to visit Churchill's resting place in Bladon.

We then ride for approximately 6 miles on small country lanes through the villages of Cassington and Yarnton before rejoining the Oxford canal path again, this time heading south. If desired by the group we can make a short 1½ mile detour to visit the grave of the Lord of the Rings author J.R.R. Tolkein.

We then head through the pretty villages of Wolvercote and Godstow. There are lovely views from here back over Port Meadow towards the city. You can see the many spires of the university college churches from here, giving the city its nickname as the “ city of dreaming spires”.

We then join the riverside path that takes us the final mile into the centre of Oxford and directly to the riverside hotel.

Elevation profile 15

Day 3

Oxford to Goring (25.7 miles)

Our first part of the day is a historic walking tour of Oxford before we set off the bikes. The tour conducted by our local guide first takes in Carfax Tower, The Covered Market, Martyrs Memorial, The Sheldonian Theatre, The Bodleian Library, The Radcliffe Camera and Radcliffe Square

We then climb the 127 steps of the tower of the University Church of St Mary the Virgin. The effort is rewarded by the most spectacular view of Oxford, looking down over Radcliffe Square, Brasenose College and All Souls College.

The walking tour continues on to: The Bridge of Sighs, The Turf Tavern, St Edmund Hall college and Magdalen College.

We then embark on a 45-minute adventure, punting in traditional wooden punts on the River Cherwell. Escape the hustle and bustle of the city as you drift peacefully along the river with its waterfowl and overhanging willow trees.

From there we set off on our bikes on river paths and country lanes until our lunch stop. The pub is right next to the churchyard where George Orwell, author of 1984 and Animal Farm, is buried.

The afternoon ride takes us 9 miles on quiet country roads, including a little hill (nothing too difficult though, and only a couple of minutes hard work) to the bustling market town of Wallingford, where you will have some free time to explore the town, visit the outdoor lido, rent a boat along the river or grab afternoon tea, before the final 6 miles to the village of Goring and our overnight accommodation. The first part of the ride is off-road along the Ridgeway, an ancient Roman route that is now a bridleway. We then finish today’s ride back on small country roads into Goring.

Elevation profile 16

Day 4

Goring to Maidenhead (37.8 miles)

We set out today along the southern bank of the Thames until the town of Caversham. Once at Caversham we will continue along the Thames riverside path through the town of Reading for 3 miles to our mid-morning tea and cake stop in Sonning.

An 8 mile ride on small roads through the Berkshire countryside to our lunch stop at the Bird Hills Golf Centre.

After lunch we head north for 4½ miles on country roads towards the village of Bray where we cross the River Thames and pick up a traffic-free bike path for the remaining 5 miles into Windsor.

Today’s highlight is a visit to Windsor Castle, home to King Charles III and resting place of the late Queen Elizabeth II. You will have 2½ hours free time in Windsor to enjoy touring the castle.

A 40-minute traffic-free ride for 6 miles following the Jubilee River on a glorious bike path that hugs the river all the way to our Thames riverside hotel in Maidenhead.

Elevation profile 17

Day 5

Maidenhead to Waddesdon (36.2 miles)

Today is probably the most challenging riding day of the tour, with a moderate amount of climbing.

We start out from Maidenhead on a greenway for 2½ miles that takes us to Cookham, where we have our first short climb.

We then ride back down to the river and cross northwards at Marlow, on a pretty suspension bridge designed by the same architect who designed the famous Széchenyi “Chain” Bridge in Budapest.

The hill out of Marlow into the Chiltern Hills, designated as an Area of Outstanding Natural Beauty, is long but not steep. The 6 mile ride is on very quiet country lanes through woodlands with beech and other trees. There are fantastic views to be seen over the Chiltern Hills once we reach the top at Lane End.

This part of the ride is finished with a fast 2 mile descent into West Wycombe, where we will visit the Hellfire Caves and stop for our morning refreshment break.

The Hellfire Caves are a cave system hewn out of the chalk underlying the Chilterns and used by a group of high-society gentlemen in the 18th century as a location for banqueting and various salacious activities, far from prying eyes.

The major hills are now behind us and we have a lovely 7 mile ride on virtually traffic-free single-track lanes.

We are very likely to see red kites flying overhead in this area. These magnificent birds of prey were nearly driven to extinction in the UK but were reintroduced in the 1990s and are now thriving. These birds soar on thermal updrafts and can have a wingspan of up to six feet.

Today’s afternoon ride takes us 7 miles along a short section of old disused railway line and then on small country lanes to the village of Haddenham, where we can take a short break on the picture-perfect village green to feed the ducks.

We then continue a further 7 miles on a mixture of local roads and traffic-free bike paths to Waddesdon.

Today’s ride involves an enjoyable finale as we plunge down into the Waddesdon estate on traffic-free roads through manicured parkland where we park the bikes at the visitor centre.

The highlight today is a visit to Waddesdon Manor. This spectacular house, built in a Neo-Renaissance style and looking like a French chateau, was built as the spectacular residence of the Rothschild family. It has been used as a filming location for many movies and television shows, including The Crown and Downton Abbey. You will have 2 hours available to visit the house and its beautiful gardens and parkland.

After the visit we have a 2-minute ride to the hotel in Waddesdon village.

Elevation profile 18

Day 6

Waddesdon to Oxford (22.7 miles)

This morning we ride for 9½ miles on single-lane country roads and bike paths to the small village of Brill in Buckinghamshire. There is a short sharp climb up to the village of no more than 10 minutes. Brill has a beautiful windmill, dating back to 1680, set on ancient earthworks. The village and surrounding landscape are said to be J.R.R. Tolkein’s inspiration for Bree, the only village in Middle Earth where men and hobbits lived together. There are beautiful views out over the countryside towards Oxford.

We leave Brill down a steep hill and onwards, once again on small country lanes for 7 miles (with the exception of a 200 yard stretch of slightly busier road) through the villages of Boarstall and Honeyburge. We have our final little hill of the day (and of the entire tour) up to the village of Stanton St John where we will stop at a pick-your-own fruit farm for our mid-morning refreshment break.

We leave Stanton St John and head 3½ miles into the Oxford suburb of Headington. If desired, a short detour can be made to visit the grave of local author C.S. Lewis (famous for the Chronicles of Narnia).

Our final ride of the tour takes us 3 miles down the hill from Headington into Oxford. We will cross over the River Cherwell on Magdalen Bridge where we went punting earlier in the tour. The tour ends back at the hotel in central Oxford where a farewell lunch will be provided. This is the official end of the tour but if desired you may go on a tour of Christ Church College, only 100 yards from the hotel.

Elevation profile 19

Route Map



The standard accommodations for this region's guided trips are small boutique hotels and luxury guesthouses. In all cases the bathroom facilities are ensuite (self-contained within the room), and the room facilities usually include a television and tea/coffee making facilities.

Breakfast is always included.

When you book a tour, your pre-trip planner will have more details about the specific facilities and services provided by the accommodations.

Examples of our hotels in this region include;

Getting here

The most convenient international airports are and London’s Heathrow Airport and Gatwick Airport.

From London Heathrow and Gatwick airports, take The Airline coach service, which runs 24 hours a day. You can also get to Oxford by train from Heathrow via London, and from Gatwick via Reading.

From London Stansted airport, take the Stansted Express train service to London Liverpool Street and then take the tube to either Paddington or Marylebone for direct trains to Oxford. Alternatively there is a National Express 737 coach service.


Direct services run from London Paddington (serving Oxford station) and London Marylebone (serving Oxford and Oxford Parkway stations). Other services operate from the north via Birmingham New Street; from the south via Reading; and from the west via Didcot or Reading.

For details and to plan your journey, see contact National Rail Enquiries.

Oxford Railway Station is a 5-10 minute walk from the centre of Oxford. Please use Google Maps or our interactive map to find your way from the station to the part of the University you are visiting.


The Oxford Tube offers a direct service between Oxford and London, running a frequent timetable on a virtually 24-hour basis, Monday to Sunday.

For information on coaches from other major cities and airports, contact National Express.

The central coach station is at Gloucester Green in the city centre.


The UK is well known for the variability of its weather – from day to day, season to season, year to year and place to place. Its position in the mid-latitude westerly wind belt on the edge of the Atlantic Ocean with its relatively warm waters, yet close to the continental influences of mainland Europe, plays a major role in this. Changes in topography and land use over relatively short distances, together with a long coastline and numerous islands, all add to the variety of weather. In general, places in the east and south of the UK tend to be drier, warmer, sunnier and less windy than those further west and north. Also, these favourable weather conditions usually occur more often in the spring and summer than in autumn and winter.

England weather is very changeable and unpredictable, but generally summers are warm and winters are cold, and temperatures are milder than those on the continent. Temperatures do not usually drop below 32°F (0°C) in winter, and in summer they hardly reach 90°F (32°C). July and August are the warmest months, while January and February is the coldest time of year. Rainfall is fairly evenly distributed throughout the year, but late winter/early spring (February to March) is the driest period.

Bicycle Rental

Hybrid Option- Scott Sub Sport 30 (or similar)- available in step through female frame.

Frame & Forks: Aluminium
Speed: 24 speed Shimano Deore
Chainset: Triple 28/38/26
Cassette: 11t – 32t
Brakes: Hydraulic disc brakes
Equipment: Rear pannier rack, mudguards, phone holder, lights, stand, front suspension and water bottle holder
Link to manufacturers website - https://www.scott-sports.com/g...

Road Bike- Scott Speedster 50

Bike Specification:

Frame & Forks: Alloy
Speed: 14 gears
Chainset: Double 50 x 34
Cassette: 7 speed 11-28
Brakes: Rim brakes
Pedals: Dual SPD (mtb) / flat pedals
Weight: 10.5 kg / 23.15 lbs

E-Bike- Gazelle Ultimate T10

Gazelle Ultimate T10 - Bike Specification:

Frame & Forks: Aluminium
Speed: 10 speed Shimano Deore
Chainset: Single 38t
Cassette: 11t – 42t
Brakes: Hydraulic disc brakes
Torque: 75 nm
Battery range: 155 km max
Motor Type: Bosch Performance Line mid-mounted
eBike sensors: Pedal force sensor, rotation sensor, speed sensor
Equipment: Rear pannier rack, phone holder, mudguards, lights, stand, front suspension and water bottle holder
Link to manufacturers website - https://www.gazellebikes.com/e...


Hi! Over the years I have enjoyed travel and have visited over 50 countries on all of the continents (except Antarctica). If you can think of it, I've probably been there!

During recent years I discovered a great love for cycling and 25,000km later after a chance meeting with The Iron Donkey team made the decision to try and turn my hobby into a career. With their backing I developed a guided tour in the area I live and know best.

I have cycled all over the world in the last 4 years with many trips in England, Scotland, Northern Ireland, Republic of Ireland, Spain, Germany, Austria, Slovakia, Hungary and Thailand. Trips to Croatia, Serbia, Malaysia and Singapore are already booked for later this year.

I have lived in Oxfordshire and Buckinghamshire for 40 years so know the area extremely well. I was educated in Oxford and currently live in a small town in the Area of Outstanding Natural Beauty that is The Chilterns Hills.

On this tour you will benefit from this local knowledge as I can take you away from the busier roads onto local, often traffic free tracks and show you many interesting "secret" points of interest as well as some of the beautiful wildlife we have here.

I am available on the below email address to answer any questions you may have about the tour and look forward to hearing from and hopefully meeting you soon.

Colin Gilbert


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