A complete guide to cycling Shaftesbury, Dorset

IF driving down the A303, go past Stonehenge and within 30 minutes you’ll be in Shaftesbury. And if taking your bike by train, jump off at Tisbury or Gillingham: both are within two hours of London.

From Tisbury, it is a beautiful, gently undulating ride past Old Wardour Castle and the sleepy hollow of Donhead St Andrew: you can then cycle south of the A30 in the lee of Win Hill and only emerge onto the main road a mile from Shaftesbury itself. It will take an hour.

The A30 from the east is the only ‘flat’ entrance into Shaftesbury. The town is built on a ridge – and all other roads, including that from Gillingham, rise steeply as you approach your destination. Which is why Shaftesbury and its hinterland is such a perfect base for a cycling holiday.

You can take the flat road east out of town into the Chalke Valley and Cranborne Chase, an Area of Outstanding Natural Beauty (AoNB). Or you can head west and south down into The Blackmore Vale, Hardy’s Vale of the Little Dairies. The views are stunning, as they are from Shaftesbury itself.

There are dozens of established routes to explore Dorset’s quiet lanes, plus the North Dorset Trailway (once a railway line) and Okeford mountain bike park with five downhill runs and lift service. Cycling for all ages and grades – and don’t forget Gold Hill….

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British Cycling is behind a scheme that qualifies Ride Leaders to accompany up to 10 cyclists at a time. Riders can be any age, but children aged 5+ should be accompanied by an adult: those under 5 can take part on a child seat or in a kiddie trailer. Colin Peck leads a gentle six-mile ride along the North Dorset Trailway, leaving Shillingstone station at 10am on the first Wednesday of each month.

There are a number of cycling clubs around Shaftesbury that also welcome visitors (see map, right). Wincanton Wheelers has rides each Saturday and Sunday – all are welcome to join. Gillingham Wheelers has an even bigger programme at weekends, as does the Blackmore Vale Cycling Club.


Dorset Adventures is based in Shaftesbury and hires three Scott models, from £25-£60 a day (including an electric E-bike), to include helmets, gloves, maps, spare inner tube and pump. ​All bikes are less than a year old, with front suspension, hydraulic disc brakes and shimano components. The company also organises half-day activities in a range of venues across Dorset, from £40pp (group of 6+), £120 family activity (family of four) or bespoke sessions from £150. And it has an introduction to mountain biking one-day course for £75pp for a group of four, or £150 for a bespoke course.

  • About 10 miles from Shaftesbury is the Okeford Hill Mountain Bike Park, which has five highly-rated downhill runs and 125m of drop. There is also an uplift service for bikes and riders at £15 a half-day or £25 a day. The park is run by Hammoon Cycles of Shaftesbury and is open on Saturdays, as well as occasional Sundays and evenings in summer (check website or Facebook page).
  • Hammoon Cycles will also hire out bikes from its shop in Shaftesbury, or will deliver locally. It also delivers bikes to Loose Reins, a riding camp with cabins near Shillingstone.


This spring, pro cyclist Ben Moore joined 400 cyclists and families on a 50-mile tour of Dorset’s lanes and byways in and around Shaftesbury, ending with a climb up the town’s legendary Gold Hill. Staged by the Rotary Club, there are 12-, 25- and 50-mile rides held on a Sunday in May, ending with food, music and drink on Park Walk, with views over The Blackmore Vale.


North Dorset Cycleway 114km

This terrific signed circular route takes you on a tour of some of the prettiest villages and finest countryside in Dorset. You will pass through the Dorset Downs and Cranborne Chase Areas of Outstanding Natural Beauty (AoNB) and the delightful Blackmore Vale. The ride starts at Gillingham railway station and heads towards the lovely town of Sturminster Newton. Situated on the River Stour the town boasts an ancient working watermill which is now a museum.

From Stur, continue to Ibberton and the fabulous Ibberton Hill with spectacular views of Dorset’s AoNB. The ride then descends to Milton Abbas where you will find pretty thatched cottages and the impressive Milton Abbas Abbey, now a school. The village is often portrayed as 36 quaint white-washed and thatched cottages each fronted by a lawn.

The next stage takes you to the market town of Blandford Forum where you cross the River Stour. Pleasant riverside sections along the Stour and the River Tarrant follow before passing through Moor Crichel, Gussage All Saints and Farnham. Here you begin a series of wooded sections through Farnham Wood and Fontmell Wood on your way to Fontmell Magna.

The next stop is Shaftesbury, the second highest market town in Britain and home to Gold Hill, a steep cobbled street featured famously on the Hovis advert. The ruined abbey, founded in 888, and its accompanying museum is also worth seeing if you have time. The final section leads you back to Gillingham via Motcombe. This route mostly takes place on country lanes and contains a few steep climbs. It is probably best to tackle it in stages unless you are an experienced cyclist.


The Trailway is a route being developed by Dorset Countryside along the old Somerset and Dorset Railway Line that closed to rail traffic in 1966. The old railway line provides an ideal cycling, walking and riding route for a Trailway as it links many of North Dorset’s towns and villages.

The largest section provides a continuous route between Blandford and Sturminster Newton, a distance of 15km, which takes you through some of North Dorset’s spectacular countryside, towns and villages with views of Hambledon Hill and the meandering River Stour. Halfway between the towns is the original station at Shillingstone, where a carriage has been converted into a dining room for the station cafe (open Weds, Sat and Sun).

An additional section is open between Blandford St Mary and Spetisbury. It is hoped one day all sections will join up to provide public access along the whole length of the old Somerset and Dorset Railway line, from Stalbridge to Spetisbury.

THE WESSEX RIDGEWAY: from Tollard Royal to the coast near Lyme Regis


Starting at Tollard Royal on the Dorset/Wiltshire border, the Dorset section of the Wessex Ridgeway meanders across the Chalk downs, climbs magnificent hillforts such as Hambledon Hill and crosses over Chalk streams brimming with wildlife.

Along the way you will pass many attractive villages such as Cerne Abbas and take in stunning views of the Blackmore and Marshwood Vales, before sauntering down through the quaint Marshwood Vale to the end of the multi-use section at Champernhayes, just north of Lyme Regis.

“The Wessex Ridgeway Trail is a magnificent ridge-top route crossing Dorset’s rural heartland. The trail offers vistas across the county and breathtaking views far beyond. The majority of the route straddles a long chalk ridge but in places is broken up by small rounded hills and secluded valleys. Each section of the trail has its own unique identity and its delights to explore,” says the Walk and Cycle website.

The Wessex Ridgeway links with a number of National Cycle Network routes. These long-distance routes include NCN routes 2, 25 and 26. They vary in length and between on and off road. The trail also links with the 253, a circular road route which links Gillingham, Shaftesbury, Farnham, Blandford Forum and Sturminster Newton.


This ride follows National Cycle route 25 through the Dorset countryside. The ride starts on the River Stour in Blandford Forum and heads north west through Stourpaine and then on to Child Okeford where you will join National Cycle route 25. The route then follows quiet country roads to Gillingham.


And don’t forget the 16% gradient of Gold Hill! There is cycling history in Shaftesbury: Samuel Baker was a cycle maker living with his wife Sarah and three children at 67 Salisbury Street, according to Kelly’s Directory (1895) and by 1935, Reg Humphries was running a cycle shop at 54B High Street.

Gold Hill has been a challenge for cyclists since the bicycle was invented 200 years ago. Gold Hill (and Ziz Zag Hill, a mile out of town,) pulls in cyclists from all over the country – the Hovis ad in 1979 magnified its reputation, further promoted by Evans Evans E-bike advert in 2017 and the enhanced Hovis ad this year.

In May this year, pro cyclist Ben Moore set a new record for cycling up the 105ft cobbled section of Gold Hill, at 22 seconds beating the previous record by three seconds. And at any other time of the year, individuals will take on their own challenge of cycling The Hill, including my friend Mickey Burke from Lincolnshire, seen below!