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Cotswolds by Bike

Cotswolds by Bike

Trip Highlights

  • Cycling Through the Heart of England
  • Quaint Stone Built Villages
  • Riding Across Rolling Hills
  • Biking Between Village Pubs and Old Coaching Inns

Trip Summary

This holiday is intended to appeal to those who want a gentle introduction to cycling in the English countryside, as the Cotswold’s are hilly rather than mountainous. A week of marvelous rides will take you through one of the most beautiful and historic parts of England. Honey coloured stone villages, open wolds, wooded valleys and Roman roads are the background to pretty villages, “wool” churches, famous gardens, a Roman villa and welcoming inns. Your tour starts in elegant Cheltenham with its Regency buildings, beautiful gardens, and fashionable centre. Then a delightful ride takes you over the top of the Wolds and through Duntisbournes, crossing the River Dunt’s pretty fords. The route passes exquisite village churches with Saxon and Norman features. This is followed by an easy ride to Tetbury, an important medieval wool market town. You can stand inside the old market house and walk down the ancient Chipping Steps - the course for the Woolsack Races. The ride then continues through the Cotswold Water Park. From Barnsley you ride along the River Coln to Bibury - described by William Morris as the most beautiful village in England - and its famous row of weavers' cottages. Then down the scenic Windrush Valley, past Windrush village’s Norman church to Burford, an elegant town with its steep main street leading down to the river. Your ride also takes you to the Eastleach villages with their fine churches and historic footbridge, and to the Barringtons. After a visit to Chedworth Roman Villa, one of the best exposed Romano-British villas in Britain, the ride takes you through Northleach, another attractive wool town with a magnificent church, to the Slaughters, surely the most delightful villages in England. You stay two nights in a superb guesthouse in Guiting Power, a typical upland Cotswold village. On the final day you will visit the historic 15th century Snowshill Manor, take lunch at Broadway and enjoy the wonderful views from Broadway Tower. In the afternoon you can visit Sudley Castle once home to three of Henry VIII's wives, Katherine Parr, Ann Boleyn and Lady Jane Grey. Finally, free wheel down Cleeve Hill back to Cheltenham.


Easy - Moderate. There is a choice of two routes each day 25 miles (moderate) or 15 miles (easy)


Make your own way to Cheltenham. Arriving early you can do a circular ride, but you must request the bike hire with Sherpa Expeditions prior to arrival. Ride 1: short ride to Churchdown Hill. Distance = 22 km/13.4 miles This is a gently undulating, easy ride until you get to Churchdown and the steep hill to St. Bartholomew’s Church; but it is worth the push up the hill - it’s peaceful, and there is a good view over the vale. Ride 2: to Deerhurst and Wainlodes via Boddington and Churchdown. Distance = 47 km/29.4 miles. This is a fairly flat and easy ride but because part of it is in the area between Gloucester and Cheltenham even the unclassified roads can be busy; the quietest area of the ride is to the west of the A38. Deerhurst is well worth visiting for its Saxon churches and Wainlodes for its magnificent view of the river Severn. Accommodation: Hanover House your 5 star guesthouse dates back to 1824, a gracious age of enlightened and generous architecture, close to Cheltenham centre and all its amenities.

Meals:  Nil

Ride 1: via Elkstone, the Duntisbournes & Daglingworth. Distance = 32 km/19.8 miles or 25.7 km/16 miles. This lovely ride is uphill at the beginning, but from Elkstone goes through easier, undulating countryside. The ride down the Duntisbourne valley is a treat. The churches at Elkstone, Duntisbourne Rouse & Daglingworth are particularly worth visiting. There are not many pub stops in the middle of the ride; you will need to visit The Green Dragon at Cockleford or the Highwayman on the A417. There are no other shops in Cheltenham. Ride 2: via Cowley, Sheepscombe, Painswick & Slad. Distance = 49 km/30.4 miles or 44 km/27.3 miles. This is an interesting, varied but hilly ride with attractive countryside and scenery and some famous towns and villages. You visit Painswick an elegant wool town, Slad, the home of Laurie Lee, the famous Cotswold author. Stroud the industrial centre of the valleys and Bisley another beautiful wool town. Although there are several steep hills the destinations are worth the effort. Accommodation: The Crown Inn is a 16th century stone inn overlooking the beautiful, wooded, Chalford Valley, your accommodation is 4 crowns.

Meals:  B

Ride 1: via South Cerney & Meysey Hampton. Distance = 35.7 km/22.2 miles or 28.15 km/17.5 miles This easy ride circles through South Cerney & the Water Park. It passes through several quiet villages & the flat south Cotswolds countryside. It finishes in Barnsley where the church & Barnsley House Garden are worth visiting. Ride 2: via Tetbury, Cherington, Ashton Keynes & Down Ampney. Distance = 53.2 km/33.1 miles. This easy ride visits Tetbury an attractive Wool town, then goes east to Ashton Keynes & the Cotswold Water Park. It goes through several quiet villages south east of Cirencester before going north back into the Cotwolds to the beautiful stone village of Barnsley. Accommodation: For two nights, the Catherine Wheel offers a warm welcome in its family-friendly 15th century Cotswold stone building with a lounge bar, restaurant, 4 star accommodation and garden.

Meals:  B

Ride 1: a short ride to Cirencester Distance = 23.65 km/14.7 miles. This easy ride goes to Cirencester via Welsh Way & Whiteway, & returns via Preston & Ampney Ride 2: Fairford via the Coln Valley & the Eastleaches. Distance = 50 km/30.6 or 41.85 km/26 miles This beautiful ride goes down the Coln Valley, which has several typical, pretty, Cotswold villages. The Woollen Mill at Filkins is interesting, & you can buy some real Cotswold souvenirs. Fairford is a good place for tea, & the stained glass windows are a must.

Meals:  B

Ride 1: via Chedworth Roman Villa, Northleach & Notgrove. Distance = 35.5 km/22.1 milies or 26 km/16.4 miles. This is an enjoyable ride over undulating countryside. The Roman Villa is very interesting, and Northleach is an attractive ’wool’ town with a lovely church. Ride 2: via the Windrush Valley, Burford, Bourton on the Water & the Slaughters. Distance = 53 km/33 miles or 43.45 km/27 miles. This is an interesting, enjoyable and fairly easy ride. It goes through many picturesque Cotswold villages - Windrush and the Slaughters are particularly delightful. Burford is an attractive town & Bourton a busy tourist centre. Accommodation: Two nights either at the Guiting Guest House a tastefully restored 16th century 4 star Cotswold stone farmhouse in the centre of a small and isolated typical Cotswold village that has allowed time to pass it by. Or the Hollow Bottom a 4 star Inn that dates back to the 17th century.

Meals:  B

Ride 1: A short ride to the Slaughters & Lower Swell. Distance = 23 km/14.3 miles This undulating ride goes through beautiful countryside & attractive quiet villages. Upper Slaughter is a lovely place to picnic & spend time by the ford on a fine day. Ride 2: to Snowshill & Chipping Campden via Blockley & Sezincote - with extensions to Broadway & Hidcote Manor Gardens. Distance = 42 km/26.3 miles, 45 km/27.9 miles or 56 km/35 miles The lovely ride goes across rolling countryside to Snowshill & Chipping Campden - two classic Cotswold towns. It can be extended to visit Broadway & Hidcote Manor Gardens. The ride is quite hilly, & even the minor roads round Chipping Campden get very busy at holiday weekends.

Meals:  B

Ride 1: via Winchcombe & Brockhampton. Distance = 28.6 km/17.8 miles or 27 km/13.5 miles This ride covers some beautiful countryside, with good views from the hills. It is quite hilly, particularly down into & up from Winchcombe, but it gives you a good knowledge of the Cotswold scarp! Winchcombe is well worth visiting, & it is easy to spend several hours there. Ride 2: via Northleach, Chedworth Roman Villa, Withington & Seven Springs. Distance = 41 km/25.5 miles. This ride goes through beautiful countryside, some attractive villages, and to Northleach - an important ’wool’ town - with an interesting ’wool’ church. The Roman Villa is fascinating. Accommodation: Your 5 star guesthouse dates back to 1824, a gracious age of enlightened and generous architecture, close to Cheltenham centre and all its amenities. Cycle hire company is located at Cheltenham train station.

Meals:  B

Trip concludes in Cheltenham after breakfast.

Meals:  B

What's Included

  • 7 breakfasts
  • 7 nights accommodation in guesthouses and hotels on a twin share basis with ensuite facilities
  • one piece of luggage per person transferred from Inn to Inn, not exceeding 20kg
  • Information pack including route notes & maps
  • Emergency hotline

What's Not Included

  • Bike hire £85
  • Dinners, lunches & beverages
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls
  • Unscheduled transfers required during the trip
  • Entrance fees

Upcoming Travel Dates


Duration:8 Days
Starting Point:Cheltenham
Finishing Point:Cheltenham
Activities:Self-Guided Cycling
Grade:Introductory to Moderate  Click for more information
Trip Code:CMR
Prices From:GBP£630 Per Person
single supplement:GBP£250  Click for more information
Single Supplement:GBP£270  Click for more information